Updated on 2024/06/22

写真a

 
ABE Takumi
 
Organization
Faculty of Medicine, Dentistry and Pharmaceutical Sciences Lecturer
Position
Lecturer
External link

Degree

  • 博士(薬学) ( 北海道大学 )

Research Interests

  • 極性転換

  • 安定等価体

  • 生理活性物質

  • 有機合成化学

  • 医薬品化学

  • 天然物化学

  • 不斉合成

  • 有機金属化学

  • 漢方

Research Areas

  • Life Science / Pharmaceutical chemistry and drug development sciences

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Life Science / Environmental and natural pharmaceutical resources

  • Humanities & Social Sciences / Archaeology

Education

  • 北海道大学大学院薬学研究科   創薬科学専攻薬品製造化学分野   博士課程

    2002.4 - 2007.3

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  • Health Sciences University of Hokkaido   薬学部  

    1998.4 - 2002.3

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Research History

  • Okayama University   学術研究院医歯薬学域   Lecturer

    2021.4

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  • Okayama University   Graduate School of Medicine , Dentistry and Pharmaceutical Sciences   Lecturer

    2020.10 - 2021.3

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    Country:Japan

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  • Health Sciences University of Hokkaido   Faculty of Pharmaceutical Sciences   Lecturer

    2019.4 - 2020.9

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  • 米国Scripps研究所   博士研究員

    2009.1 - 2009.8

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  • Health Sciences University of Hokkaido   Faculty of Pharmaceutical Sciences   Assistant Professor

    2007.4 - 2019.3

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Professional Memberships

 

Papers

  • Switchable Synthesis of 3-Aminoindolines and 2’-Aminoarylacetic Acids Using Grignard Reagents and 3-Azido-2-hydroxyindolines Reviewed

    Toshiki Yamashiro, Takumi Abe

    Chemical Communications   2024.5

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    <jats:p>The switchable synthesis of 3-aminoindolines and 2’-aminoaryl acetic acids from the same substrates, 3-azido-2-hydroxyindolines, was developed through denitogenative electrophilic amination of Grignard reagents. The key to success is the serendipitous...</jats:p>

    DOI: 10.1039/d4cc01448k

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  • Synthetic strategies for the construction of C3–N1′ bisindoles Reviewed

    Takumi Abe

    Organic & Biomolecular Chemistry   2024.1

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    Authorship:Lead author, Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/D3OB02089D

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  • Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences Reviewed

    Koji Yamada, Tetsu Tsubogo, Hikaru Kanazawa, Sayaka Ishizuka, Koutaro Ohyama, Masaki Kaida, Takumi Abe

    European Journal of Organic Chemistry   2023.12

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/ejoc.202301130

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  • Total Synthesis of the Proposed Structure of Indolyl 1,2-Propanediol Alkaloid, 1-(1H-Indol-3-yloxy)propan-2-ol Invited Reviewed

    Momoko Kimata, Takumi Abe

    Chemistry   2023.12

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    Authorship:Last author, Corresponding author   Publishing type:Research paper (scientific journal)  

    DOI: 10.3390/chemistry5040177

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  • On Demand Synthesis of C3-N1' Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of (±)-Rivularin A. Reviewed International journal

    Keisuke Tokushige, Takumi Abe

    Chemistry (Weinheim an der Bergstrasse, Germany)   e202302963   2023.11

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    In this work, a straightforward synthesis of C3-N1' bisindolines is achieved by a formal umpolung strategy. The protocols were tolerant of a wide variety of substituents on the indole and indoline ring. In addition, the C3-N1' bisindolines could be converted to C3-N1' indole-indolines and C3-N1'-bisindoles. Also, we have successfully synthesized (±)-rivularin A through a biomimetic late-stage tribromination as a key step.

    DOI: 10.1002/chem.202302963

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  • Oxytrofalcatin Puzzle: Total Synthesis and Structural Revision of Oxytrofalcatins B and C Reviewed

    Kazuma Sugitate, Toshiki Yamashiro, Ibuki Takahashi, Koji Yamada, Takumi Abe

    The Journal of Organic Chemistry   88 ( 14 )   2023.7

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.3c00691

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  • One-Pot Synthesis of Core Structure of Shewanelline C Using an Azidoindoline Reviewed

    Toshiki Yamashiro, Keisuke Tokushige, Takumi Abe

    The Journal of Organic Chemistry   88 ( 6 )   3992 - 3997   2023.3

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.joc.3c00013

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  • Aluminum-Catalyzed Cross Selective C3–N1′ Coupling Reactions of N-Methoxyindoles with Indoles Invited Reviewed

    Keisuke Tokushige, Toshiki Yamashiro, Seiya Hirao, Takumi Abe

    Chemistry   5 ( 1 )   452 - 462   2023.3

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:MDPI AG  

    C3–N1′ bond formation of bisindoles has been a great challenge due to the intrinsic reactivity of indoles as both C3 and N1-nucleophilic character. Herein, we demonstrate an C3–N1′ cross-coupling reaction of indoles using N-methoxyindoles as N-electrophilic indole reagents in the presence of Lewis acid. The bisindoles generated in this transformation are latent C3-nucleophile, allowing them to be used as strategic intermediates in sequential C3–N1′–C3′–N1″ triindole formations. The potential synthetic usefulness of this sequential transformation was highlighted upon application to the construction of C3–N1 looped polyindoles.

    DOI: 10.3390/chemistry5010033

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  • Revisiting Cryptocyanine Dye, NK-4, as an Old and New Drug: Review and Future Perspectives Reviewed

    Shihui Liu, Toshihiko Matsuo, Takumi Abe

    International Journal of Molecular Sciences   24 ( 5 )   2023.2

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    Authorship:Last author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.3390/ijms24054411

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  • Synthesis of Spiro[indole-3,3′-pyrrolidine]-2′-(thi)ones Reviewed

    Motohiro Yasui, Haruna Ohbu, Maho Ishikawa, Tatsuhito Yoshida, Norihiko Takeda, Seiya Hirao, Takumi Abe, Masafumi Ueda

    The Journal of Organic Chemistry   88 ( 2 )   1093 - 1106   2023.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.joc.2c02561

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  • Outstanding Reviewers for RSC Advances in 2022

    Takumi Abe

    RSC Advances   2023

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/D3RA90053C

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  • Traditional Chinese Medicines and Prescriptions Brought from China to Japan by a Monk (Jianzhen, Japanese: Ganjin): A Historical Review Invited Reviewed

    Shihui Liu, Toshihiko Matsuo, Chie Matsuo, Takumi Abe

    Compounds   2 ( 4 )   267 - 284   2022.10

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:MDPI AG  

    (1) Background: Japanese Kampo medicine has its origin in ancient Chinese medicine. In 742, a Tang Dynasty monk named Jianzhen (Ganjin) was invited by Japanese clerics to visit Japan and teach commandments in Buddhism. Because of the dangers of the voyage and also other obstacles, he took 11 years to reach Japan on the sixth voyage and he was blind when he arrived in Japan. He was the first person in China to go to Japan to establish the Buddhism commandments, and he was also the first person in Japan to directly teach traditional Chinese medicine. Until now, there have been few reports in English about the details of the Chinese herbal medicines he brought to Japan, including the types of herbal medicines, pharmacological activities, and formulations. In the review, we systematically and comprehensively summarized Jianzhen’s life from the standpoint of his medical and pharmaceutical knowledge and the types and pharmacological activities of Chinese herbal medicines and prescriptions that were brought to Japan by Jianzhen; (2) Methods: A review was made on the relevant literature written by Chinese, Japanese, and English languages regarding the medical and pharmacological knowledge of Jianzhen, the 36 Chinese herbal medicines brought to Japan by Jianzhen, and the pharmacological and therapeutic effects of these 36 herbal medicines, as well as their formulations; (3) Results: The review of the literature proved that Jianzhen’s prescriptions served as a basis for current herbal medicines (Kampo) in Japan. In the process of the literature search, we found a book entitled Jianshangren (Holy Priest Jianzhen)’s Secret Prescription, which recorded the complete prescription of the 36 traditional Chinese medicines Jianzhen brought to Japan; (4) Conclusions: Jianzhen is one of the ancestors of traditional Chinese medicine/Kampo medicine, and he brought traditional Chinese medicine and medical books to Japan for patients. He made important contributions to the development of traditional Chinese medicine in Japan.

    DOI: 10.3390/compounds2040022

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  • First Total Synthesis of Reassigned Echinosulfonic Acid D Reviewed

    Takumi Abe, Ren Nakajima, Toshiki Yamashiro, Daisuke Sawada

    Journal of Natural Products   85 ( 8 )   2022.8

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society ({ACS})  

    DOI: 10.1021/acs.jnatprod.2c00559

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  • Outstanding Reviewers for Organic & Biomolecular Chemistry in 2021

    Takumi Abe

    Organic & Biomolecular Chemistry   20 ( 28 )   5499 - 5499   2022.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Organic &amp; Biomolecular Chemistry  

    <jats:p>We would like to take this opportunity to highlight the Outstanding Reviewers for <jats:italic>Organic &amp; Biomolecular Chemistry</jats:italic> in 2021, as selected by the editorial team for their significant contribution to the journal.</jats:p>

    DOI: 10.1039/D2OB90069F

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  • Indole Editing Enabled by HFIP-Mediated Ring-Switch Reactions of 3-Amino-2-Hydroxyindolines Reviewed

    Abe, T., Yamashiro, T., Shimizu, K., Sawada, D.

    Chemistry - A European Journal   28 ( 37 )   2022.5

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    Authorship:Lead author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/chem.202201113

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  • Chemo- and Site-Selective Replacement of N-Terminal Carbamates in Peptides Reviewed

    Miho Ibara, Takumi Abe, Daisuke Sawada

    Organic Letters   2022.3

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  • Synthesis of 2-monosubstituted indolin-3-ones by cine-substitution of 3-azido-2-methoxyindolines Invited Reviewed

    Toshiki Yamashiro, Takumi Abe, Daisuke Sawada

    Organic Chemistry Frontiers   9 ( 7 )   1897 - 1903   2022.2

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

    We have developed an efficient reaction of 3-azido-2-methoxyindolines with <italic>O</italic>-nucleophiles in the presence of a Lewis acid, affording 2-monoacyloxy or alkoxy indolin-3-ones.

    DOI: 10.1039/D2QO00048B

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  • Cis-3-Azido-2-Methoxyindolines as Safe and Stable Precursors to Overcome the Instability of Fleeting 3-Azidoindoles Reviewed International journal

    Toshiki Yamashiro, Takumi Abe, Masaru Tanioka, Shinichiro Kamino, Daisuke Sawada

    Chemical Communications   57 ( 98 )   13381 - 13384   2021.11

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    Use of 3-azidoindoles in organic synthesis remains difficult task owing to their instabilities. Herein, we report a general and concise approach for tackling this problem by using 3-azidoindole surrogates. The...

    DOI: 10.1039/d1cc06033c

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  • Synthesis of α-substituted indolylacetamide using acetonitriles as acetamide enolate equivalents through O-transfer reactions. Reviewed International journal

    Takumi Abe, Kenta Noda, Daisuke Sawada

    Chemical communications (Cambridge, England)   57 ( 61 )   7493 - 7496   2021.7

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    We introduce readily available ammonium hemiaminals as O-transfer reagents and commercially available acetonitriles as a primary amide enolate precursor. The combination serves as an amide enolate equivalent, thereby providing one-pot access to α-substituted indolylacetamides. A broad substrate scope and good functional group tolerance as well as gram-scale synthesis make this protocol highly attractive. Mechanistic experiments suggest that the cyano group is trapped by a hydroxy group of hemiaminals en route to the desired primary amides under metal-free conditions.

    DOI: 10.1039/d1cc02821a

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  • A metal-, oxidant-, and fluorous solvent-free synthesis of alpha-indolylketones enabled by an umpolung strategy Reviewed

    Takumi Abe, Seiya Hirao, Toshiki Yamashiro

    CHEMICAL COMMUNICATIONS   56 ( 70 )   10183 - 10186   2020.9

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

    Enamines undergo alpha-indolization with ammonium salts in the presence of Et3N to form alpha-indolylketones. This is the first example of transition metal-, oxidant-, and fluorous solvent-free alpha-indolization of ketones. Key to the success of this convenient protocol was the use ofin situgenerated electrophilic indole species, as well as the use of enamines as a ketone enolate equivalent.

    DOI: 10.1039/d0cc04795c

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  • レセルピンの立体化学表記の訂正

    Takumi Abe

    ファルマシア   2020.8

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    Authorship:Last author, Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)  

    DOI: 10.14894/faruawpsj.56.8_757

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  • Rapid access to indole-fused bicyclo[2.2.2]octanones by merging umpolung strategy and molecular iodine as a green catalyst Reviewed

    Takumi Abe

    Organic & Biomolecular Chemistry   2020.5

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    <p>One-pot synthesis of indole-fused bicyclo[2.2.2]octanones from DiMeOIN and 2-cyclohexen-1-one are accomplished under iodine catalyst. This simple and metal-free conditions provides a practical tool to construct Csp3-rich complex molecules via oxidative...</p>

    DOI: 10.1039/d0ob01038c

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  • Revisiting 2-Alkoxy-3-bromoindolines: Control C-2 vs. C-3 Elimination for Regioselective Synthesis of Alkoxyindoles. Reviewed

    Takumi Abe, Yuta Kosaka, Takaaki Kawasaki, Yuki Ohata, Toshiki Yamashiro, Koji Yamada

    Chemical & pharmaceutical bulletin   68 ( 6 )   555 - 558   2020

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    The regioselective synthesis of both 2- and 3-alkoxyindoles from a common intermediate, 2-alkoxy-3-bromoindolines (ROBIN), is described. The 2-alkoxyindoles are obtained by a base-promoted regioselective elimination of HBr from ROBIN, whereas the synthesis of 3-alkoxyindoles is achieved by a silver-mediated alkoxylation followed by an acid-promoted elimination of alkoxide. This key elimination features the complete regioselectivity and no need for catalysts, that makes it have potential synthetic applications. Furthermore, this protocol is user friendly because ROBIN is able to be prepared from commercially available indoles and is a bench-stable easy-to-handle crystalline substrate, thus allowing the concise synthesis of a variety of both 2- and 3-alkoxyindoles.

    DOI: 10.1248/cpb.c20-00135

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  • 2,3-Dimethoxyindolines: a latent electrophile for SNAr reactions triggered by indium catalysts Reviewed

    Seiya Hirao, Toshiki Yamashiro, Kyouka Kohira, Naoki Mishima, Takumi Abe

    Chemical Communications   2020

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    Authorship:Last author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

    DOI: 10.1039/D0CC01210F

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  • A Mild Bischler–Napieralski-Type Cyclization of Trichloromethyl Carbamates for the Synthesis of β-Carbolinones Reviewed

    Takumi Abe

    HETEROCYCLES   101 ( 1 )   2020

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.3987/com-19-s(f)19

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  • Development and Application of Indole-2,3-epoxide Surrogates Reviewed

    Abe Takumi, Yamada Koji, Nishi Takahide

    Journal of Synthetic Organic Chemistry, Japan   78 ( 6 )   597 - 607   2020

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    Authorship:Lead author, Corresponding author   Language:Japanese   Publisher:The Society of Synthetic Organic Chemistry, Japan  

    <p>C3-Nucleophilic substitution of indoles has been limited because the transformation requires an umpolung of the C3 position of indoles. Among the indole derivatives, indole-2,3-epoxides could be potentially be used as C3-electrophilic reagents due to the electrophilic nature of the C2 and C3 positions. However, their use as C3 electrophilic reagents has not been possible so far due to their instability.</p><p>We describe a novel and bench stable surrogate of indole-2,3-epoxide, 2-hydroxyindoline-3-triethylammonium bromide (HITAB), which was found to be a convenient reagent for formal C3-electrophilic reactions of indoles with nucleophiles. By taking advantage of the nucleophilic character of the oxygen of the 2-hydroxyindoline, interrupted retro-Claisen and interrupted Feist-Bénary reactions with 1,3-dicarbonyl compounds, one-pot formation of furodiindolines from 3-substituted indoles were achieved. Furthermore, we developed a novel cascade reaction of the indole-2,3-epoxide surrogate with γ-carbolines to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-<i>a</i>]indoles. This reaction utilizes the <i>in situ</i> formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences. The synthetic potential of the ammonium salts was demonstrated by the short synthesis of cryptolepine, iheyamine A, racemocine B derivative, and neocryptolepine derivative.</p>

    DOI: 10.5059/yukigoseikyokaishi.78.597

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  • Rapid access to indole-fused bicyclo[2.2.2]octanones by merging the umpolung strategy and molecular iodine as a green catalyst

    Abe, T., Hirao, S.

    Organic and Biomolecular Chemistry   18 ( 22 )   2020

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    DOI: 10.1039/d0ob01038c

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  • Rapid access to indole-fused bicyclo[2.2.2]octanones by merging the umpolung strategy and molecular iodine as a green catalyst

    Takumi Abe, Seiya Hirao

    Organic & Biomolecular Chemistry   18 ( 22 )   2020

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    Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

    DOI: 10.1039/D0OB01038C

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  • Silver-Mediated Intramolecular Friedel–Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines: Synthesis of Isochromeno[3,4-b] indolines and 3-Arylindoles Reviewed

    Toshiki Yamashiro, Koji Yamada, Haruka Yoshida, Yutaro Tomisaka, Takahide Nishi, Takumi Abe

    Synlett   30 ( 20 )   2247 - 2252   2019.11

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    © 2019 Georg Thieme Verlag. All rights reserved. We disclose a silver-mediated intramolecular Friedel-Crafts-type cyclization of 2-benzyloxy-3-bromoindolines to afford an untapped family of isochromeno[3,4-b[indolines and 3-arylindoles, in which deformylative arylation of 2-(4-methoxybenzyloxy)-3-bromoindolines is reported for the first time. The isochromeno[3,4-b[indolines can be readily transformed into other heterocyclic moieties.

    DOI: 10.1055/s-0039-1690734

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  • Total Synthesis of Fontanesine B and Its Isomer: Their Antiproliferative Activity against Human Colorectal Cancer Cells Reviewed International journal

    Takumi Abe

    Helvetica Chimica Acta   102 ( 7 )   2019.6

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/hlca.201900116

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  • Total Synthesis of Proposed Structure of Azepinobisindole Alkaloid Rhodozepinone Reviewed

    Takumi Abe

    HETEROCYCLES   98 ( 6 )   2019.5

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    DOI: 10.3987/com-19-14077

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  • Revisiting Furodiindolines: One-Pot Synthesis of Furodiindolines Using Indole 2,3-Epoxide Surrogates and Their Synthetic Applications Reviewed

    Takumi Abe, Sakura Aoyama, Masami Ohmura, Masato Taniguchi, Koji Yamada

    Organic Letters   21 ( 9 )   3367 - 3371   2019.4

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    Authorship:Lead author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.9b01108

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  • Direct C4-Benzylation of Indoles via Tandem Benzyl Claisen/Cope Rearrangements Reviewed

    Takumi Abe, Yuta Kosaka, Miku Asano, Natsuki Harasawa, Akane Mishina, Misato Nagasue, Yuri Sugimoto, Kazuaki Katakawa, Shunsuke Sueki, Masahiro Anada, Koji Yamada

    Organic Letters   21 ( 3 )   826 - 829   2019.2

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    Authorship:Lead author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society ({ACS})  

    DOI: 10.1021/acs.orglett.8b04120

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  • Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy Reviewed

    Tomoki Itoh, Yuusuke Chiba, Shunsuke Kawaguchi, Yuki Koitaya, Yuuma Yoneta, Koji Yamada, Takumi Abe

    RSC Advances   9 ( 18 )   10420 - 10424   2019

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    Authorship:Last author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

    <p>The regioselective synthesis of pyrano[3,2-<italic>e</italic>]indole alkaloid fontanesine B have been accomplished by C4 Pictet–Spengler cyclization and Bischler–Napieralski-type cyclization of a trichloromethyl carbamate.</p>

    DOI: 10.1039/C9RA02321F

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  • Biomimetic Synthesis of Iheyamine A from Spirocyclic Oxindoles Reviewed

    Takumi Abe, Koji Yamada, Syuhei Satake

    HETEROCYCLES   99 ( 0 )   379 - 379   2019

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    Authorship:Lead author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Japan Institute of Heterocyclic Chemistry  

    DOI: 10.3987/com-18-s(f)30

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  • Double "open and Shut" Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds Reviewed

    Takumi Abe, Haruka Shimizu, Shiori Takada, Takahiro Tanaka, Mai Yoshikawa, Koji Yamada

    Organic Letters   20 ( 6 )   1589 - 1592   2018.3

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society  

    A novel cascade reaction of indole-2,3-epoxide equivalents with γ-carbolines by utilizing a double "open and shut" transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences.

    DOI: 10.1021/acs.orglett.8b00332

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  • Dehydrative Mannich-Type Reaction for the Synthesis of Azepinobisindole Alkaloid Iheyamine A Reviewed

    Takumi Abe, Koji Yamada

    Organic Letters   20 ( 5 )   1469 - 1472   2018.3

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society  

    A concise synthesis of the azepinobisindole alkaloid iheyamine A from an indole-2,3-epoxide equivalent has been achieved. This method features a formal C3 electrophilic reaction of an indole-2,3-epoxide equivalent with tryptamine to form a 3-aminoindoline and a novel In-catalyzed dehydrative Mannich-type reaction of the hemiaminal to give the azepinobisindole core.

    DOI: 10.1021/acs.orglett.8b00330

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  • Synthesis of Phaitanthrin E and Tryptanthrin through Amination/Cyclization Cascade Reviewed

    Takumi Abe, Masaru Terasaki

    Helvetica Chimica Acta   101 ( 2 )   e1700284   2018.2

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley Blackwell  

    Phaitanthrin E was biomimetically synthesized from methyl indole-3-carboxylate and methyl anthranilate or anthranilic acid using the ester group as an activating group. The reaction proceeds through NCS-mediated dearomatization/TFA-catalyzed protonation of indolenine/C(2) amination/Et3N-promoted aromatization and cyclization in one-pot procedure. This method is capable of converting simple biomass materials to phaitanthrin E. The synthesis not only allows assessment of antiproliferative activity, but also affords experimental support for the hypothetical biosynthetic pathway of phaitanthrin E. The resulting phaitanthrin E derivatives were evaluated for in vitro antiproliferative activity against human colorectal cancer cells (DLD-1). The biogenetic intermediate of phaitanthrin E showed higher antiproliferative activity than the natural product, phaitanthrin E. Furthermore, a concise synthesis of tryptanthrin is also accomplished from indole-3-carbaldehyde and methyl anthranilate using the aldehyde group as an activating group.

    DOI: 10.1002/hlca.201700284

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  • Radical Cyclizations of Aryl Bromides for Synthesis of Cyclopenta[b]Indoles from Vince Lactam Reviewed

    Takumi Abe, Tsuyoshi Morita, Koji Yamada

    HETEROCYCLES   97 ( 0 )   141 - 141   2018

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  • Nazarov cyclization of an indolyl vinyl ketone promoted by acetyl chloride and sodium iodide: Formal synthesis of Bruceolline e Reviewed

    Takumi Abe

    Heterocycles   96 ( 3 )   490 - 500   2018

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    An acetyl chloride/NaI-mediated Nazarov-type cyclization of an indolyl vinyl ketone was developed to give a cyclopenta[b]indole in high yield. An acyl Finkelstein reaction is a key feature for this unprecedented Nazarov-type cyclization.

    DOI: 10.3987/COM-18-13866

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  • Synthesis of Indoloquinazoline Alkaloids Using Cascade Reactions Reviewed

    Abe Takumi

    Journal of Synthetic Organic Chemistry, Japan   76 ( 8 )   802 - 809   2018

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    <p>We describe the total synthesis of indolo[2,1-b]quinazoline alkaloids tryptanthrin (1a), candidine (2), phaitanthrins A (3), B (4), C (5), cruciferane (8), and cephalanthrin A (9) using oxidative cascade sequences as the key step. Phaitanthrin E (7a) was synthesized by a novel methodology that features a concise approach involving the intermolecular condensation and intramolecular aryl C-H amination mediated by Cu-complexes to construct the indolo[2,1-b]quinazoline core. Moreover, an acid catalyzed one-pot synthesis of phaitanthrin E (7a) via intermolecular amination/intramolecular cyclization cascade using NCS was also developed.</p>

    DOI: 10.5059/yukigoseikyokaishi.76.802

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  • An Ullmann N-arylation/2-amidation cascade by self-relay copper catalysis: one-pot synthesis of indolo[1,2-a]quinazolinones Reviewed

    Takumi Abe, Yuka Takahashi, Yuki Matsubara, Koji Yamada

    ORGANIC CHEMISTRY FRONTIERS   4 ( 11 )   2124 - 2127   2017.11

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    We have developed a self-relay copper(I)-catalyzed Ullmann N-arylation/2-amidation cascade to form functionalized indolo[1,2-a]quinazolinones in one-pot from easily available indoles with 2-bromobenzamides. This novel transformation features a tandem process of Ullmann-type coupling, activation of indolenine, and 2-amidation in the presence of a single copper catalyst. In addition, among the substituents of indoles at the C3 position, methyl carboxylate could act as an activating group in this Ullmann N-arylation/2-amidation cascade.

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  • C4 Pictet-Spengler Reactions for the Synthesis of Core Structures in Hyrtiazepine Alkaloids Reviewed

    Takumi Abe, Tomohiro Haruyama, Koji Yamada

    SYNTHESIS-STUTTGART   49 ( 18 )   4141 - 4150   2017.9

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    The hyrtiazepine alkaloids are a family of bisindole natural products that have the azepinoindole backbone. We developed a biomimetic approach by constructing the azepinoindole core in a one-pot manner through 1,4-diazabicyclo[2.2.2]octane/2,2,2-trifluoroethanol (DABCO/TFE) promoted Pictet-Spengler reaction onto the C-4 position of tryptophan. This strategy allowed the synthesis of common key structures of these families. The key intermediate can be converted into the 3H-pyrano[2,3-b:5,6-e']diindol intermediate present in hyrtimomines A and B, as well as the azepinoindole core present in fargesine.

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  • 2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles Reviewed

    Takumi Abe, Takuro Suzuki, Masahiro Anada, Shigeki Matsunaga, Koji Yamada

    ORGANIC LETTERS   19 ( 16 )   4275 - 4278   2017.8

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    A novel indole-2,3-epoxide equivalent, 2-hydroxyindbline-3-triethylammonium bromide, was found, to be a convenient reagent for formal C3-electrophilic reactions of indoles with various nudeophiles. By taking advantage of the nudeophilie character of the oxygen of the 2-hydroxyindo-line the interrupted retro-Claisen interrupted Feist - Benary reactions, with 1,3-dicarbonyl compounds Were efficiently achieved.

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  • A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines Reviewed

    Takumi Abe, Koshiro Kida, Koji Yamada

    CHEMICAL COMMUNICATIONS   53 ( 31 )   4362 - 4365   2017.4

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    We have developed a copper-catalyzed Ritter-type reaction/cyclization cascade of anthranilic acids and nitriles, affording the quinazolin-4(3H)-ones. The cascade proceeds through a Ritter-type reaction capturing the iminoketene intermediates by nitriles. Furthermore, we found a novel Ritter-type reaction/condensation/intramolecular anti-Markovnikov hydroamination cascade, providing access to functionalized diazocines in one-pot.

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  • Concise Syntheses of Hyrtioreticulins C and D via a C-4 Pictet-Spengler Reaction: Revised Signs of Specific Rotations Reviewed

    Takumi Abe, Koji Yamada

    JOURNAL OF NATURAL PRODUCTS   80 ( 2 )   241 - 245   2017.2

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    The first syntheses of hyrtioreticulins C and D via a Pictet Spengler reaction at the C-4 position of the indole rings are described. The synthesis proceeds in only two steps from commercially available starting materials. In this Communication, the structures of the natural products were confirmed. Furthermore, we revise the signs of the specific rotations of hyrtioreticulins C and D.

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  • One-pot synthesis of fused 2-pyridones from heteroarylacrylic acid via curtius rearrangement &amp; microwave-assisted thermal electrocyclization Reviewed

    Takashi Nishiyama, Noriyuki Hatae, Kaori Hayashi, Manami Obata, Kimiko Taninaka, Masahiro Yamane, Shota Oda, Takumi Abe, Minoru Ishikura, Satoshi Hibino, Tominari Choshi

    Heterocycles   95 ( 1 )   251 - 267   2017

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    ©2017 The Japan Institute of Heterocyclic Chemistry. We investigated the one-pot synthesis of several fused 2-pyridone ring systems based on a Curtius rearrangement, followed by a microwave-assisted thermal electrocyclization of a 2-aza-6?-electron system including isocyanate. We synthesized seven heterocyclic compounds containing a fused 2-pyridone ring. In these results, the one-pot synthesis of fused 2-pyridone ring system 5 from (E)-acrylic acids 1 under microwave irradiation conditions was more effective than the conventional reaction conditions in terms of the yield and the reaction time.

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  • SYNTHESIS OF (+/-)-CEPHALANTHRIN A USING BAEYER-VILLIGER OXIDATION

    Takumi Abe

    Heterocycles   95 ( 1 )   2017

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    DOI: 10.3987/COM-16-S(S)5

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  • Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E Reviewed

    Takumi Abe, Koji Yamada

    ORGANIC LETTERS   18 ( 24 )   6504 - 6507   2016.12

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    We have developed a concise one-pot synthesis of phaitanthrin E derivatives, where simple starting materials undergo an acid-catalyzed intermolecular amination/intramolecular cyclization cascade.

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  • Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells Reviewed

    Takashi Nishiyama, Noriyuki Hatae, Teruki Yoshimura, Sawa Takaki, Takumi Abe, Minoru Ishikura, Satoshi Hibino, Tominari Choshi

    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY   121   561 - 577   2016.10

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    We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O-2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types. (C) 2016 Elsevier Masson SAS. All rights reserved.

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  • Synthesis of (±)-Cephalanthrin A using Baeyer-Villiger Oxidation

    Takumi Abe

    Heterocycles   2016.6

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  • A ONE-POT SYNTHESIS OF PHAITANTHRIN E THROUGH INTERMOLECULAR CONDENSATION/INTRAMOLECULAR ARYL C-H AMINATION CASCADE Reviewed

    Tomoki Itoh, Takumi Abe, Tominari Choshi, Takashi Nishiyama, Minoru Ishikura

    HETEROCYCLES   92 ( 6 )   1132 - 1136   2016.6

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    A one-pot synthesis of phaitanthrin E starting from methyl indole-3-carboxylate and isatoic anhydride through intermolecular condensation/intramolecular aryl C-H amination cascade was developed.

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    Other Link: http://orcid.org/0000-0003-1729-1097

  • Concise Total Syntheses of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6 pi-Electrocyclization Reviewed

    Tomoki Itoh, Takumi Abe, Tominari Choshi, Takashi Nishiyama, Reiko Yanada, Minoru Ishikura

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2016 ( 13 )   2290 - 2299   2016.5

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    Concise syntheses of 9-methoxyellipticine, 3,4-dihydroellipticine (mu-alkaloid D), 1,2,3,4-tetrahydroellipticine, 2-methyl-1,2,3,4-tetrahydroellipticine, olivacine, 3,4-dihydroolivacine, (+/-)-guatambuine, and (+/-)-janetine were developed starting from hexatriene intermediates readily obtained by Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborates. The route enables the facile construction of pyrido[4,3-b]carbazoles by Cu-catalyzed 6 pi-electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4,3-b]carbazole alkaloids.

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  • TOTAL SYNTHESIS OF CARBAZOLE-1,4-QUINONE ALKALOID KOENIGINEQUINONES A AND B BASED ON A ONE-POT CYCLOCARBONYLATION PROCEDURE FROM 2-ALKENYL-3-IODOINDOLE Reviewed

    Takashi Nishiyama, Nanase Satsuki, Satoshi Hibino, Mami Fujii, Takumi Abe, Minoru Ishikura, Tominari Choshi

    HETEROCYCLES   93 ( 1 )   84 - 100   2016.4

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    Total syntheses of koeniginequinones A and B, isolated from Murraya koenigii, were newly achieved by constructing of carbazole-1,4-quinone using a one-pot Pd-catalyzed cyclocarbonylation method with 2-(but-2-en-l-y1)-3-iodoindoles derived from known methyl 6-methoxyindole-2-carboxylate and methyl 5,6-dimethoxyindole-2-carboxylate, followed by desilylation, and an oxidation sequence.

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  • Palladium-catalyzed cross-coupling reaction of indolylborates and its application for the syntheses of indole alkaloids Reviewed

    Takumi Abe, Minora Ishikura

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   74 ( 2 )   117 - 129   2016

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    In our continuing study of the reactivity and synthetic application of indolylborate as a versatile synthetic intermediate, we found that the use of indolylborate in palladium-catalyzed cross -coupling reaction is highly effective for the synthesis of indole derivatives. The present account deals with the results concerning a novel approach to indole alkaloids based on the use of the palladium-catalyzed cross-coupling. Dimeric indole alkaloid, yuechuke, was synthesized through the palladium-catalyzed carbonylative cross-coupling reaction. Pyridocarbazole alkaloids (ellip-ticine, olivacine, and their related alkaloids), and indolophenanthridine alkaloid (calothrixins A and B) were obtained by the use of cyclization/cross-coupling domino reaction. In addition, (CuOTf) 2 toluene complex was demonstrated to catalyze 6π-electrocyclization of hexatrienes, leading to pyrido [4,3-b] carbazoles.

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  • Cu-MEDIATED OXIDATIVE DIMERIZATION OF SKATOLE TO TRYPTANTHRIN, AN INDOLO[2,1-b]QUINAZOLONE ALKALOID Reviewed

    Tomoki Itoh, Takumi Abe, Shuhei Nakamura, Minoru Ishikura

    HETEROCYCLES   91 ( 7 )   1423 - 1428   2015.7

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    A one-pot conversion of skatole to tryptanthrin, an indolo[2,1-b]quinazoline alkaloid, was achieved by Cu-mediated oxidation.

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  • Pd-CATALYZED INTRAMOLECULAR OXIDATIVE COUPLING REACTION OF 1,1 '-CARBONYLDIINDOLES

    Takumi Abe, Minoru Ishikura

    HETEROCYCLES   90 ( 1 )   673 - 680   2015.1

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    The palladium-catalyzed intramolecular oxidative coupling reaction of 1,1'-carbonyldiindoles was achieved by using Pd(OAc)(2) and Cu(OAc)(2), producing 1,1'-carbonyl-2,2'-biindolyls, which were then converted to tjipanazoles D and I

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  • Simple indole alkaloids and those with a nonrearranged monoterpenoid unit Reviewed

    Minoru Ishikura, Takumi Abe, Tominari Choshi, Satoshi Hibino

    NATURAL PRODUCT REPORTS   32 ( 10 )   1389 - 1471   2015

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    This review covers the literature on simple indole alkaloids and those with a nonrearranged monoterpenoid unit from the beginning of 2012 up to the end of 2013, which includes newly isolated alkaloids, structure determinations, total syntheses and biological activities.

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  • N-Substituted calothrixin B derivatives inhibited the proliferation of HL-60 promyelocytic leukemia cells Reviewed

    Noriyuki Hatae, Risa Satoh, Hitomi Chiba, Takahiro Osaki, Takashi Nishiyama, Minoru Ishikura, Takumi Abe, Satoshi Hibino, Tominari Choshi, Chiaki Okada, Eiko Toyota

    MEDICINAL CHEMISTRY RESEARCH   23 ( 11 )   4956 - 4961   2014.11

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    Calothrixin B, whose structure consists of a pentacyclic indolo[3,2-j] phenanthridine framework, was originally isolated as a secondary metabolite from Calothrix cyanobacteria and was found to exhibit potent antiproliferative activity. In this study, treatment with 100 mu M of calothrixin B did not inhibit the proliferation of HL-60 promyelocytic leukemia cells, the result indicated that calothrixin B could possess weaker activity against leukemia cells. In a previous study of the structure-antiproliferative activity relationships of calothrixin B analogs, the tetracyclic 5H-pyrido[4,3-b] carbazole-4,11(6H)-dione structure, which does not include the benzene ring found in calothrixin B, was reported to be necessary for antiproliferative activity; however, the induction of substituents on the indole nitrogen atom of calothrixin B decreased the antiproliferative activity of the compound. To develop calothrixin B analogs with good antiproliferative activity against both HL-60 and HCT-116 cells, we synthesized various N-substituted calothrixin B analogs and assessed their activity. Compared with calothrixin B, N-OMe calothrixin B displayed almost the same or slightly stronger antiproliferative activity against HCT-116 cells, whereas the N-MOM analog demonstrated slightly weaker activity against these cells. These two analogs also inhibited proliferation of HL-60 cells, whereas calothrixin B did not exhibit antiproliferative activity toward these cells. Among calothrixin B analogs, N-OMe and N-MOM calothrixins B are cytotoxic against HCT-116 cells and not the lack of the effect on HL-60 cells.

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  • One-pot synthesis of tryptanthrin by the Dakin oxidation of indole-3-carbaldehyde Reviewed

    Takumi Abe, Tomoki Itoh, Tominari Choshi, Satoshi Hibino, Minoru Ishikura

    TETRAHEDRON LETTERS   55 ( 38 )   5268 - 5270   2014.9

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    A one-pot approach to indolo[2,1-b]quinazolines from indole-3-carbaldehydes through the Dakin oxidation was developed. It was shown that the reaction proceeded through the condensation of indole-3-carbaldehydes with isatoic anhydrides, derived in situ from indole-3-carbaldehydes by the Dakin oxidation, and further oxidation/cyclization steps. (C) 2014 Elsevier Ltd. All rights reserved.

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  • A novel one-pot synthesis of carbazole-1,4-quinones through Pd-catalyzed cyclocarbonylation, desilylation and oxidation processes from 3-iodo-2-propenylindoles Reviewed

    Mami Fujii, Takashi Nishiyama, Tominari Choshi, Nanase Satsuki, Takaya Fujiwaki, Takumi Abe, Minoru Ishikura, Satoshi Hibino

    TETRAHEDRON   70 ( 9 )   1805 - 1810   2014.3

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    novel one-pot synthesis of carbazole-1,4-quinone by consecutive Pd-catalyzed cyclocarbonylation, desilylation, and oxidation reactions is described. We propose a possible mechanism of the cyclocarbonylation reaction between 3-iodo-2-propenylindole and CO (1 atm) in the presence of a tributyl(vinyl)tin and Pd-catalyst and the resulting acylpalladium species was directly coupled with a terminal alkene to produce the carbazole-1,4-quinone. To our knowledge, this is the first example of this type of reaction. A new formal total synthesis of a carbazole-1,4-quinone alkaloid, murrayaquinone A was established using this reaction. (C) 2014 Elsevier Ltd. All rights reserved.

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  • ONE-POT ACCESS TO 3,3 '-BISINDOLYLMETHANES THROUGH THE INTERMOLECULAR PUMMERER REACTION Reviewed

    Takumi Abe, Toshiaki Ikeda, Tomoki Itoh, Noriyuki Hatae, Eiko Toyota, Minoru Ishikura

    HETEROCYCLES   88 ( 1 )   187 - 191   2014.1

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    A one-pot synthesis of 3,3'-bisindolylmethanes was developed through the intermolecular Pummerer reaction using indole as a nucleophile.

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  • Effect of the orthoquinone moiety in 9,10-phenanthrenequinone on its ability to induce apoptosis in HCT-116 and HL-60 cells Reviewed

    Noriyuki Hatae, Jun Nakamura, Tetsuo Okujima, Minoru Ishikura, Takumi Abe, Satoshi Hibino, Tominari Choshi, Chiaki Okada, Hiroko Yamada, Hidemitsu Uno, Eiko Toyota

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   23 ( 16 )   4637 - 4640   2013.8

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    9,10-Phenanthrenequinone (9,10-PQ) is one of the most abundant quinones among diesel exhaust particulates. Recent data have suggested that quinones induce apoptosis in immune, epithelial and tumor cells, leading to respirator illness; however, the mechanisms by which quinones induce apoptosis and the structure required for this remain unknown. We studied the antitumor activity of 9,10-PQ analogs against two human tumor cell lines, HCT-116 colon tumor cells and HL-60 promyelocytic leukemia cells. The loss of the cis-orthoquinone unit in 9,10-PQ abrogated its ability to induce apoptosis in the two tumor cell lines, and the LC50 values of these analogs were indicated over 10 mu M. An analog of 9,10-PQ in which the biaryl unit had been deleted displayed a reduced ability to induce tumor cell apoptosis, while the analogs 1,10-phenanthroline-5,6-dione (9) and pyrene-4,5-dione (10), which also had modified biaryl units, exhibited increased tumor cell apoptotic activity. The cis-orthoquinone unit in 9,10-PQ was identified as essential for its ability to induce apoptosis in tumor cells, and its biaryl unit is also considered to influence orthoquinone-mediated apoptotic activity. (C) 2013 Elsevier Ltd. All rights reserved.

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  • Biomimetic transamination of α-keto esters Reviewed

    Takumi Abe

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   71 ( 1 )   62 - 63   2013.7

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    The development of biomimetic reactions is one of the major challenges for synthetic chemists, because mimicking these complicated reactions in the laboratory by simple catalytic systems is difficult to achieve in general. Vitamine B6-dependent aminotransferase-catalyzed transamination of α-keto acids from pyridoxamine is an important process to generate α-amino acids in nature. In this review, recent progresses on the biomimetic transamination of α-keto esters are described.

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  • One-pot construction of 3,3′-bisindolylmethanes through Bartoli indole synthesis Reviewed

    Takumi Abe, Shuuhei Nakamura, Reiko Yanada, Tominari Choshi, Satoshi Hibino, Minoru Ishikura

    Organic Letters   15 ( 14 )   3622 - 3625   2013.7

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    A one-pot approach to 3,3′-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3′-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH 4Cl. © 2013 American Chemical Society.

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  • Simple indole alkaloids and those with a non-rearranged monoterpenoid unit Reviewed

    Minoru Ishikura, Takumi Abe, Tominari Choshi, Satoshi Hibino

    NATURAL PRODUCT REPORTS   30 ( 5 )   694 - 752   2013

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    This review covers the literature on simple indole alkaloids and those with a non-rearranged monoterpenoid unit from the beginning of 2010 up to the end of 2011, which includes newly isolated alkaloids, structure determinations, total syntheses and biological activities.

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  • Synthesis of indole compounds using multifunctional synthons Reviewed

    Takumi Abe

    Yakugaku Zasshi   133 ( 1 )   99 - 106   2013

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    This review describes a synthesis of indole compounds using multifunctional synthons. The multifunctional synthons, trienes and gramines, were respectively synthesized using Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborate with vinyl bromide, and reaction of indolylcuprate with iminium chloride. As an application of the multifunctional synthons to the indole alkaloids synthesis, we accomplished the total synthesis of ellipticine, 9-methoxyellipticine, 9-hydroxyellipticine, tetrahydroellipticine, μ-alkaloid B, μ-alkaloid D, calothrixin A, calothrixin B, tubifoline, and yuehchukene. We have also developed 6π-electrocyclization of hexatrienes catalyzed by Cu(I) trifluoromethanesulfonate toluene complexe, which is unprecedented. © 2013 The Pharmaceutical Society of Japan.

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  • SHORT APPROACH TO BISINDOLE ALKALOID, YUEHCHUKENE, USING 2-INDOLYLCYANOCUPRATE

    Takumi Abe, Hiroyuki Komatsu, Toshiaki Ikeda, Noriyuki Hatae, Eiko Toyota, Minoru Ishikura

    HETEROCYCLES   86 ( 1 )   505 - 513   2012.12

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    A short total synthesis of a bisindole alkaloid, yuechukene, was achieved through the dimerization of beta-dehydroprenylindole generated in situ from 1-(indol-3-yl)-3-methylbut-2-en-1-amine.

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  • Total Synthesis of Calothrixins A and B by Palladium-Catalyzed Tandem Cyclization/Cross-Coupling Reaction of Indolylborate

    Takumi Abe, Toshiaki Ikeda, Tominari Choshi, Satoshi Hibino, Noriyuki Hatae, Eiko Toyata, Reiko Yanada, Minoru Ishikura

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2012 ( 26 )   5018 - 5027   2012.9

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    The palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indol-2-yl)borate with vinyl bromide was successfully used in the concise total synthesis of the indolophenanthridine alkaloids, calothrixins A and B.

    DOI: 10.1002/ejoc.201200657

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  • Synthesis and antimalarial activity of calothrixins A and B, and their N-alkyl derivatives Reviewed

    Kohji Matsumoto, Tominari Choshi, Mai Hourai, Yoshito Zamami, Kenji Sasaki, Takumi Abe, Minoru Ishikura, Noriyuki Hatae, Tatsunori Iwamura, Shigeo Tohyama, Junko Nobuhiro, Satoshi Hibino

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   22 ( 14 )   4762 - 4764   2012.7

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    We synthesized calothrixin B using our developed biomimetic method and derived N-alkyl-calothrixins A and B. The in vitro antimalarial activity of the calothrixin derivatives, including calothrixins A and B, against the Plasmodium falciparum FCR-3 strain was evaluated. All test compounds exhibited antimalarial activity over a concentration range of 6.4 x 10(-6)-1.2 x 10(-7) M. (C) 2012 Elsevier Ltd. All rights reserved.

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  • Concise Total Synthesis of Calothrixins A and B Reviewed

    Takumi Abe, Toshiaki Ikeda, Reiko Yanada, Minoru Ishikura

    ORGANIC LETTERS   13 ( 13 )   3356 - 3359   2011.7

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    The concise total synthesis of calothrixins A and B has been accomplished by utilizing the one-pot formation of hexatriene as a key intermediate via the palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indo1-2-yl)borate. In another key transformation, the indolo[3,2-j]phenanthridine core was prepared in high yield via Cu(I)-mediated 6 pi-electrocyclization.

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  • FACILE SYNTHESIS OF PYRANO[3,2-e]INDOLES VIA THE BASE-PROMOTED PICTET-SPENGLER REACTION OF N-b-BENZYLSEROTONIN

    Koji Yamada, Sayaka Yamaguchi, Noriyuki Hatae, Takumi Abe, Tatsunori Iwamura, Minoru Ishikura

    HETEROCYCLES   83 ( 4 )   815 - 826   2011.4

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    A novel and simple protocol for the synthesis of 1-(2-aminoethyl)pyrano[3,2-e]indole derivatives has been developed using the Pictet-Spengler reaction of N-b-benzylserotonin with alpha,beta-unsaturated aldehydes in the presence of Et3N in 2-propanol or MeOH.

    DOI: 10.3987/COM-11-12144

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  • Metal-Catalyzed Reactions between 2-Azabicyclo[2.2.1]hept-5-en-3-ones and Arylboronic Acids Reviewed

    Takumi Abe, Hiroyuki Takeda, Yumi Takahashi, Yoshihisa Miwa, Koji Yamada, Minoru Ishikura

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2010 ( 17 )   3281 - 3294   2010.6

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    Cu- and Rh-catalyzed coupling reactions of 2-azabicyclo[2.2.1]hept-5-en-3-ones (1) with arylboronic acids were successful carried out under microwave irradiation conditions and yielded N-aryl and C-aryl derivatives of 1, respectively.

    DOI: 10.1002/ejoc.201000135

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  • Copper-Catalyzed Ritter-Type Reaction of Unactivated Alkenes with Dichloramine-T

    Takumi Abe, Hiroyuki Takeda, Yoshihisa Miwa, Koji Yamada, Reiko Yanada, Minoru Ishikura

    HELVETICA CHIMICA ACTA   93 ( 2 )   233 - 241   2010

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    It was shown that dichloramine-T (1) reacted with cyclohexene in acetonitrile to give N&apos;-(2-chlorocyclohexyl) amidine 2a and N-(2-chlorocyclohexyl)acetamide (3) via the competitive addition of acetonitrile and N-chloro-N-tosylamino anion to cyclohexenechloronium ion. This reaction can be catalyzed by Cu(OAc)(2), primarily affording 2a. Furthermore, the resulting 2a can be cyclized to benzimidazol 14a in good yield by treating with KOH in dioxane.

    DOI: 10.1002/hlca.200900214

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  • Simple indole alkaloids and those with a nonrearranged monoterpenoid unit Reviewed

    Minoru Ishikura, Koji Yamada, Takumi Abe

    NATURAL PRODUCT REPORTS   27 ( 11 )   1630 - 1680   2010

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    This review covers the literature on simple indole alkaloids and those with a nonrearranged monoterpenoid unit, and includes newly isolated alkaloids, structure determinations, total syntheses and biological activities.

    DOI: 10.1039/c005345g

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  • Revisiting AI-2 Quorum Sensing Inhibitors: Direct Comparison of Alkyl-DPD Analogues and a Natural Product Fimbrolide Reviewed

    Colin A. Lowery, Takumi Abe, Junguk Park, Lisa M. Eubanks, Daisuke Sawada, Gunnar F. Kaufmann, Kim D. Janda

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   131 ( 43 )   15584 - +   2009.11

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    Quorum sensing (QS) systems have been discovered in a wide variety of bacteria, and mediate both intra- and interspecies communication. The AI-2-based QS system represents the most studied of these proposed interspecies systems and has been shown to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the study of unknown AI-2-based QS systems and the potential treatment of bacterial infections. The fimbrolide class of natural products has exhibited excellent inhibitory activity against AI-2-based QS and as such may be considered the "gold standard" of AI-2 inhibitors. Thus, we sought to include a fimbrolide as a control compound for our recently developed alkyl-DPD panel of AI-2 modulators. Herein, we present a revised synthesis of a commonly studied fimbrolide as well as a direct comparison between the fimbrolide and alkyl-DPD analogues. We demonstrate that our alkyl-DPD analogues are more potent inhibitors of QS in both Vibrio harveyi and Salmonella typhimurium, the two organisms with defined AI-2 QS systems, and in doing so call into question the widely accepted use of fimbrolide-derived compounds as the "gold standard" of AI-2 inhibition.

    DOI: 10.1021/ja9066783

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  • REACTION OF N-beta-BENZYLSEROTONIN WITH alpha,beta-UNSATURATED AND ARYL ALDEHYDES IN THE PRESENCE OF A BASE Reviewed

    Koji Yamada, Yuichi Namerikawa, Takumi Abe, Minoru Ishikura

    HETEROCYCLES   77 ( 2 )   825 - 828   2009.2

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    The reaction of N-beta-benzylserotonin with alpha,beta-unsaturated and aryl aldehydes in the presence of a base produced 1H-azepino[5,4,3-cd]indoles.

    DOI: 10.3987/COM-08-S(F)98

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  • RHODIUM-CATALYZED ARYLATION OF 2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE WITH ARYLBORONIC ACIDS UNDER MICROWAVE IRRADIATION Reviewed

    Takumi Abe, Hiroyuki Takeda, Yumi Takahashi, Yoshihisa Miwa, Koji Yamada, Minoru Ishikura

    HETEROCYCLES   75 ( 12 )   2931 - 2936   2008.12

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    Rhodium-catalyzed arylation of 2-azabicyclo[2.2.1]hept-5-en-3-one was successfully performed by applying microwave irradiation.

    DOI: 10.3987/COM-08-11483

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  • A concise approach to (+/-)-tubifoline based on the palladium-catalyzed cross-coupling reaction of indolylborate Reviewed

    Minoru Ishikura, Norinobu Takahashi, Koji Yamada, Takumi Abe

    HETEROCYCLES   75 ( 1 )   107 - 118   2008.1

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    The palladium-catalyzed tandem cyclization-cross-coupling protocol using 1H-indol-2-yltrialkylborate (indolylborate) proved to be a versatile approach to the generation of 2-(4-piperidylmethyl)indole, which was successfully used for the preparation of (+/-)-tubifoline.

    DOI: 10.3987/COM-07-11190

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  • Formal Synthesis of Olivacine via Indolylborate Reviewed

    Minoru Ishikura, Norinobu Takahashi, Koji Yamada, Takumi Abe, Reiko Yanada

    HELVETICA CHIMICA ACTA   91 ( 10 )   1828 - 1837   2008

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    Palladium-catalyzed tandem cyclization - cross-coupling reaction of indolylborate 2 and vinyl bromide 5 was successfully applied in a short formal synthesis of olivacine. The reaction of 2 with 5 in the presence of Pd(OAc)(2) readily afforded three kinds of products, triene derivative 6 and vinylindole derivative 7, along with a small amount of the piperidine derivative 8 (Scheme 2). On the other hand, the reactions of 2 with bromide 10 or 15 were also examined (Schemes 4 and 5) and their outcome markedly depended oil the relative ease of ring closure as a function of ring size. Irradiation of 6 with a high-pressure pressure mercury lamp (-9; Scheme 2), followed by removal of the N-[(benzyloxy)carbonyl] group and subsequent oxidation afforded, after deprotection, pyridocarbazole 23, and the conversion of 23 to olivacine is known (Scheme 6).

    DOI: 10.1002/hlca.200890195

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  • Copper-catalyzed N-arylation reaction of 2-azabicyclo[2.2.1]hept-5-en-3-one with arylboronic acids under microwave irradiation Reviewed

    Takumi Abe, Hiroyuki Takeda, Koji Yamada, Minoru Ishikura

    Heterocycles   76 ( 1 )   133 - 136   2008

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    Copper-catalyzed N-arylation reaction of 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) with arylboronic acids was successively performed in the presence of KOH and trimethylamine-N-oxide under microwave irradiation. © The Japan Institute of Heterocyclic Chemistry.

    DOI: 10.3987/COM-07-S(N)6

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  • Asymmetric syntheses of diarylheptanoid natural products (-)-centrolobine and (-)-de-O-methylcentrolobine via hetero-Diels-Alder reaction catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate] Reviewed

    Takuya Washio, Reika Yamaguchi, Takumi Abe, Hisanori Nambu, Masahiro Anada, Shunichi Hashimoto

    TETRAHEDRON   63 ( 48 )   12037 - 12046   2007.11

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    Catalytic asymmetric syntheses of (-)-centrolobine and (-)-de-O-methylcentrolobine have been achieved, incorporating a hetero-Diels-Alder (HDA) reaction between 4-aryl-2-silyloxy-1,3-butadienes and phenylpropargyl aldehyde derivatives as a key step. The HDA reaction using dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh-2(R-BPTPI)(4), as a chiral Lewis acid catalyst provides exclusively cis-2,6-disubstituted tetrahydropyran-4-ones in up to 93% ee. (C) 2007 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2007.09.003

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  • Catalytic enantioselective Amination of silyl enol ethers using chiral Dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine Reviewed

    Masahiro Anada, Masahiko Tanaka, Takuya Washio, Minoru Yamawaki, Takumi Abe, Shunichi Hashimoto

    ORGANIC LETTERS   9 ( 22 )   4559 - 4562   2007.10

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    [GRAPHICS]
    Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh-2(S-FPTTL)(4), is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or a,beta-enones with [N-(2-nitrophenyisulfonyl)imino]phenyliodinane (NsN=IPh), providing N-(2-nitrophenyisulfonyl)-alpha-amino ketones in high yields and with enantioselectivities of up to 95% ee. The effectiveness of the present catalytic protocol has been demonstrated by an asymmetric formal synthesis of (-)-metazocine.

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  • Catalytic enantioselective aziridination of alkenes using chiral dirhodium(II) carboxylates Reviewed

    Minoru Yamawaki, Masahiko Tanaka, Takumi Abe, Masahiro Anada, Shunichi Hashimoto

    HETEROCYCLES   72   709 - 721   2007.4

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    The enantioselective aziridination of alkenes with [N-(4-nitrophenylsulfonyl)imino]phenyliodinane catalyzed by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh-2(S-TCPTTL)(4), is described. While such enantioselectivities are highly dependent on the properties of the alkenes, 2,2-dimethylchromene was found to be a particularly suitable substrate which can be efficiently transformed into the aziridine product in 98% yield with 94% ee.

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  • Catalytic enantioselective tandem carbonyl ylide formation/1,3-dipolar cycloaddition reactions of alpha-diazo ketones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-valinate] Reviewed

    Hideyuki Tsutsui, Naoyuki Shimada, Takumi Abe, Masahiro Anada, Makoto Nakajima, Seiichi Nakamura, Hisanori Nambu, Shunichi Hashimoto

    ADVANCED SYNTHESIS & CATALYSIS   349 ( 4-5 )   521 - 526   2007.3

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    The first successful example of the enantioselective intermolecular 1,3-dipolar cycloaddition of a chiral dirhodium(II) catalyst-associated carbonyl ylide with an aromatic aldehyde dipolarophile is described. The tandem carbonyl ylide formation/cycloaddition reactions of 1-diazo-5-aryl-2,5-pentanediones with aromatic aldehydes using dirbodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-valinate] as a catalyst provide exclusively exo cycloadducts in up to 92% ee.

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  • Investigation of the regioselectivity on the reaction of 2-indolylcyanocuprate with N-(prop-2-en-1-ylidene)aminium chloride derivatives Reviewed

    Minoru Ishikura, Hiroyuki Komatsu, Koji Yamada, Takumi Abe, Reiko Yanada

    HETEROCYCLES   71 ( 11 )   2325 - 2329   2007

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    Regioselectivity on the reaction of (1-methylindol-2-yl)cyanocuprate with N-(prop-2-en-1-ylidene)aminium chlorides was investigated.

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  • Practical synthesis of dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate] Reviewed

    H Tsutsui, T Abe, S Nakamura, M Anada, S Hashimoto

    CHEMICAL & PHARMACEUTICAL BULLETIN   53 ( 10 )   1366 - 1368   2005.10

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    An efficient and reliable procedure for the preparation of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh-2(S-PTTL)(4), a universally effective catalyst for a range of enantioselective carbene transformations, is described. The N-phthaloylation of (S)-tert-leucine by the method of Bose with essentially no racemization is a key to this process.

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  • 極性転換型インドール試薬を用いたC3-N1'ビスインドール骨格の構築

    徳重慶祐, 阿部 匠

    複素環化合物討論会講演要旨集 52th   2023.10

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  • Identification and evaluation of a compound that specifically inhibits oxidative modification of IRE1α

    黒木春那, ZHANG Kam Y.J., 阿部匠, 澤田大介, 上原孝

    日本薬学会年会要旨集(Web)   143rd   2023

  • Characterization of a specific inhibitor of DNMT3B S-nitrosylation

    伊藤嘉崇, 山元黎奈, 野村亮輔, 阿部匠, 澤田大介, 上原孝

    日本薬学会年会要旨集(Web)   143rd   2023

  • Development and application of indolyl azide equivalents based on the stabilization by O-Nβ bonding

    山城寿樹, 阿部匠, 谷岡卓, 神野伸一郎, 澤田大介

    日本薬学会年会要旨集(Web)   142nd   2022

  • Synthesis of 2-arylindoles by the dehydrative skeletal rearrangement and its application

    清水香帆, 阿部匠, 谷岡卓, 神野伸一郎, 澤田大介

    日本薬学会年会要旨集(Web)   142nd   2022

  • アジドインドリンの開発とその応用

    山城寿樹, 阿部匠, 谷岡卓, 神野伸一郎, 澤田大介

    反応と合成の進歩シンポジウム講演要旨集   48th   2022

  • ベンゾチアゾール連結型大環状化合物の合成研究

    和久夢, 木全桃子, 阿部匠, 澤田大介

    反応と合成の進歩シンポジウム講演要旨集   47th   2021

  • 二重極性転換型インドール試薬の開発と芳香族求核置換反応への応用

    平尾誠弥, 阿部匠, 澤田大介

    反応と合成の進歩シンポジウム講演要旨集   47th   2021

  • Synthesis of benzothiazole-linked polycyclic compounds via intramolecular C-H bond activation - cyclization and application to macrocyclic compounds

    和久夢, 阿部匠, 澤田大介

    日本薬学会年会要旨集(Web)   141st   2021

  • Synthesis of Indolyacetamides by Alkylation・Cyclization・O-Transfer Reactions

    阿部匠, 野田健太, 澤田大介

    日本薬学会年会要旨集(Web)   141st   2021

  • チオアミドを用いたペプチドN末端カルバメート保護基変換反応の開発

    茨実穂, 阿部匠, 澤田大介

    反応と合成の進歩シンポジウム講演要旨集   47th   2021

  • 多金属ヒドリドクラスター インドールの極性転換 Bpy触媒 Z型配位子

    島 隆則, 阿部 匠, 尾西 尚弥, 姫田 雄一郎, 稲垣 冬彦

    有機合成化学協会誌   78 ( 6 )   637 - 637   2020

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    DOI: 10.5059/yukigoseikyokaishi.78.637

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  • Development of practical synthesis of spiro[indole-3,3’-pyrrolidone]

    安井基博, 石川真帆, 吉田龍仁, 武田紀彦, 平尾誠弥, 阿部匠, 上田昌史

    日本薬学会年会要旨集(CD-ROM)   140th   2020

  • Synthesis of Isochromeno[3,4-b]indolines by Intramolecular Friedel-Crafts-Type Cyclizations

    山城寿樹, 山田康司, 吉田悠, 冨坂祐太朗, 西剛秀, 阿部匠

    日本薬学会年会要旨集(CD-ROM)   140th   2020

  • フォンタネシンBの初全合成

    伊藤智貴, 阿部匠, 寺崎将, 山田康司

    日本薬学会年会要旨集(CD-ROM)   139th   2019

  • Benzyl Claisen/Cope転位を経由する4-ベンジル-2-オキシインドールの合成

    山田康司, 小坂祐太, 浅野未来, 原澤夏希, 三品茜, 永末みさと, 杉本有里, 片川和明, 末木俊輔, 穴田仁洋, 阿部匠

    反応と合成の進歩シンポジウム講演要旨集   45th   2019

  • One-pot synthesis of fused 2-pyridones from heteroarylacrylic acid via Curtius rearrangement and microwave- assisted thermal electrocyclization

    36   37 - 37   2018.12

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  • 構造活性相関 分子ローター カスケード反応 有機電界効果トランジスタ(OFET)特性

    渡辺 匠, 清尾 康志, 阿部 匠, 片桐 洋史

    有機合成化学協会誌   76 ( 8 )   851 - 851   2018

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    Language:Japanese   Publisher:公益社団法人 有機合成化学協会  

    DOI: 10.5059/yukigoseikyokaishi.76.851

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  • アンモニウム塩とガンマカルボリンを用いるカスケード反応の開発

    阿部匠, 清水遥, 高田志緒里, 田中崇大, 吉川舞, 山田康司

    反応と合成の進歩シンポジウム講演要旨集   44th   2018

  • 酸化銅を用いたジベンゾジアゾシンのワンポット合成

    阿部匠, 木田恒志郎, 山田康司

    日本薬学会年会要旨集(CD-ROM)   138th   2018

  • アゼピノインドールアルカロイドの短工程合成研究

    山田康司, 阿部匠

    日本薬学会年会要旨集(CD-ROM)   138th   2018

  • Phaitanthrin E異性体の合成

    高橋侑加, 松原裕希, 山田康司, 阿部匠

    日本薬学会年会要旨集(CD-ROM)   138th   2018

  • オルト効果を利用したインドロ[1,2-a]キナゾリノン簡便合成法の開発

    阿部匠, 高橋侑加, 松原裕希, 山田康司

    複素環化学討論会講演要旨集   48th   2018

  • Iheyamine Aの全合成

    山田康司, 阿部匠

    反応と合成の進歩シンポジウム講演要旨集   44th   2018

  • Ullmannアリール化/2-アミド化カスケード反応の開発

    松原裕希, 高橋侑加, 山田康司, 阿部匠

    日本薬学会年会要旨集(CD-ROM)   138th   2018

  • P2-16 Developement of Indole-2,3-epoxide Equivalent and Synthesis of Antimalarial Cryptolepine

    Yamada Koji, Abe Takumi

    Symposium on the Chemistry of Natural Products, symposium papers   60   583-588   2018

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    DOI: 10.24496/tennenyuki.60.0_583-588

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  • A One-pot Synthesis of Phaltanthrin E Through Intermolecular Condensation/Intramolecular Aryl C-H Amination Cascade

    35   38 - 38   2017.12

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  • Total Synthesis of Carbazole-1,4-quinone Alkaloid Koeniginequinones A and B based on a One-Pot Cyclocarbonylation Procedure from 2-Alkenyl-3-iodoindole

    35   41 - 41   2017.12

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  • Concise Total Synthesis of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6冗-Electrocyclization

    35   37 - 37   2017.12

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  • Concise Synthesis of Carbazole-1,4-quinons and Evaluation of Thier Antiproliferative Activity against HCT-116 and HL-60 Cells

    35   39 - 39   2017.12

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  • SYNTHESIS OF (±)-CEPHALANTHRIN A USING BAEYER-VILLIGER OXIDATION (Dedicated to Professor Dr. Masakatsu Shibasaki on the occasion of his 70th birthday)

    Heterocycles : an international journal for reviews and communications in heterocyclic chemistry   95 ( 1 )   507 - 516   2017.1

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  • アゼピノインドール骨格の簡便合成とアルカロイド合成への応用

    山田康司, 阿部匠

    複素環化学討論会講演要旨集   47th   2017

  • インドール-3-カルボン酸メチルの2-アミノ化/環化カスケード反応の開発

    阿部匠, 山田康司

    複素環化学討論会講演要旨集   47th   2017

  • P-43 Synthesis of Azepinoindole Allaloids via a C-4 Pictet-Spengler Reaction

    Yamada Koji, Abe Takumi

    Symposium on the Chemistry of Natural Products, symposium papers   59   405 - 410   2017

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    Clavicipitic acid (1), aurantioclavine (2), fargesine (3), cimitrypazepine (4),
    hyrtiazepine (5), hyerimomine A-C (6-8), hyrtinadines C, D (9, 10) and hyrtioleticulins C, D
    (11, 12) are a unique family of indole alkaloids characterized by a novel
    azepino[5,4,3-cd]indole ring system. In our continuing interest in the synthesis of indole
    alkaloids, we have developed a biomimetic approach by constructing the
    azepino[5,4,3-cd]indole in a one-pot manner through the base promoted C-4 Pictet-Spengler reaction of Nb-benzylserotonin (13) or 5-hydroxytryptophan methyl ester (19) with aldehydes. This strategy allowed the synthesis of common key structures of azepinoindole
    families.
    A concise synthesis of aurantioclavine (5) was accomplished in only three steps from
    Nb-benzylserotonin (13) and aldehyde 20 by using this strategy. The reaction of 13 with 20
    in the presence of Et3N in MeOH, followed by treatment with Tf2O provided azepinoindole 29 in 60% yield. Subsquentry, conversion of 29 to 2 was achived via catalytic reduction.
    Recentry, we reported the first synthesis of the azepinoindole alkaloid hyrtioreticulins
    C and D (11, 12) through a C-4 Pictet-Spengler reaction between 5-hydroxytryptophan
    methyl ester (19) and acetaldehyde (21). The C-4 Pictet-Spengler reaction using DIEA in
    MeOH was carried out under microwave irradiation, and allowed to give trans-25a and
    cis-25b in 59% and 4% yield, respectively. The methyl esters 25 were subjected to
    hydrolysis and gave hyrtioreticulins C and D (11, 12) in 70-72% yield.
    On the other hand, the reaction of 19 with indole-3-carbaldehyde 22 was successful in
    the presence of DABCO in TFE, leading to 26 in 85% yield. The removal of Ts and Bn
    group were performed by Mg/MeOH and H2/Pd-C provided 32 in 50%. Further
    transformation to 5 was failed due to instability of 32 under oxidation conditions.
    Further studies directed to the synthesis of other azepinoindole alkaloids with the use of
    base-promoted C-4 Pictet-Spengler reaction are in progress.

    DOI: 10.24496/tennenyuki.59.0_405

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  • インドレニンの酸触媒活性化を利用したphaitanthrin Eの簡便合成

    阿部匠, 山田康司

    日本薬学会年会要旨集(CD-ROM)   137th   2017

  • インドロキノリン骨格の簡便合成

    山田康司, 阿部匠

    日本薬学会年会要旨集(CD-ROM)   137th   2017

  • Ritter型カスケード反応を用いるキナゾリノンとジアゾシンの簡便合成

    阿部匠, 木田恒志郎, 山田康司

    反応と合成の進歩シンポジウム講演要旨集   43rd   2017

  • インドール-2,3-エポキシド等価体の合成と求核試薬との反応

    山田康司, 鈴木拓郎, 穴田仁洋, 松永茂樹, 阿部匠

    反応と合成の進歩シンポジウム講演要旨集   43rd   2017

  • Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

    ( 34 )   33 - 33   2016.12

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  • Concise Total Syntheses of Indolo[2,1-b]quinazoline alkaloids

    Abe Takumi, Itoh Tomoki, Taguchi Ryo, Ishikura Minoru

    Symposium on the Chemistry of Natural Products, symposium papers   58 ( 0 )   Poster11   2016

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    <p> Tryptanthrin (1a), a indolo[2,1-b]quinazoline alkaloid with a potent antitumor activity, was isolated from the culture of fungus Candida lipolytica. Several related alkaloids, such as candidine (2), phaitanthrins A (3), B (4), C (5), D (6), E (7), cruciferane (8), and cephalanthrin A (9) have also been found in a wide range of natural sources. Because their diverse biological activities and structural intricacy, these alkaloids have been the target numerous synthetic studies. We envisaged oxidative dimerization of indoles for the construction of these indolo[2,1-b]quinazoline. Herein, we describe the total synthesis of indolo[2,1-b]quinazoline alkaloids tryptanthrin (1a), candidine (2), phaitanthrins A (3), B (4), C (5), E (7), cruciferane (8), and cephalanthrin A (9) using oxidative dimerization of indoles or amination/condensateion cascade as the key step.</p><p> After intensive investigations, we found that urea hydrogen peroxide (UHP) prompted dimerization of indole-3-carbaldehyde (10a) to tryptanthrin (1a) in good yields, while other oxidants did not cause this dimerization at all. In addition, oxidative dimerization of skatole (11a) via C-H oxidation, afforded 1a, could proceed in the presence of CuI and PCC. </p><p> Next, the conversion of 1a to phaitanthrins A (3), B (4), C (5) cruciferane (8), and cephalanthrin A (9) could be carried out. In the course of their synthesis, the unprecedented one-pot formation of candidine (2) via trimerization of 10a in the presence of UHP and a catalytic amount of (PhSe)<sub>2</sub> was also observed. </p><p> Phaitanthrin E (7) was also synthesized by a novel methodology that features a concise approach involving the intermolecular condensation and intramolecular aryl C-H amination mediated by Cu-complexes to construct the indolo[2,1-b]quinazoline core. In the key Cu-mediated condensation/amination cascade, a combination of CuI and Et<sub>3</sub>N turned out to effect conversion of methyl indole-3-carboxylate (15) to phaitanthrin E (7) in one-pot protocol. Moreover, the acid catalyzed one-pot synthesis of phaitanthrin E (7) via intermolecular aryl C-H amination/intramoecular cyclization cascade using NCS was also developed. </p>

    DOI: 10.24496/tennenyuki.58.0_Poster11

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  • スカトールのC-H酸化反応を経由するtryptanthrinの合成

    阿部匠, 伊藤智貴, 石倉稔

    日本薬学会年会要旨集(CD-ROM)   136th   2016

  • (±)-セファランスリンAの簡便合成

    伊藤智貴, 阿部匠, 石倉稔

    複素環化学討論会講演要旨集   46th   2016

  • Baeyer-Villiger転位反応を用いた(±)-cephalanthrin Aの合成

    伊藤智貴, 阿部匠, 石倉稔

    日本薬学会年会要旨集(CD-ROM)   136th   2016

  • スカトールの酸化的二量化反応によるインドロキナゾロンのワンポット合成

    阿部匠, 伊藤智貴, 仲村修平, 石倉稔

    反応と合成の進歩シンポジウム講演要旨集   41st   2015

  • 新規タンデムDakin酸化反応によるtryptanthrinの簡便合成

    阿部匠, 伊藤智貴, 石倉稔

    日本薬学会年会要旨集(CD-ROM)   135th   2015

  • ラン科植物アルカロイドphaitanthrin Eの合成研究

    伊藤智貴, 阿部匠, 石倉稔

    日本薬学会年会要旨集(CD-ROM)   135th   2015

  • Tryptanthrin類の簡便合成

    伊藤智貴, 阿部匠, 石倉稔

    複素環化学討論会講演要旨集   45th   2015

  • Effect of the orthoquinone moiety in 9,10-phenanthrenequinone on the ability to induce in HCT-116 and HL-60 cells.

    ( 32 )   18 - 19   2014.12

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    9,10-Phenanthrenequinone (9,10-PQ) is one of the most abundant quinones among diesel exhaust particulates. Recent data have suggested that quinones induce apoptosis in immune, epithelial and tumor cells, leading to respirator illness; however, the mechanisms by which quinones induce apoptosis and the structure required for this remain unknown. We studied the antitumor activity of 9,10-PQ analogs against two human tumor cell lines, HCT-116 colon tumor cells and HL-60 promyelocytic leukemia cells. The loss of the cis-orthoquinone unit in 9,10-PQ abrogated its ability to induce apoptosis in the two tumor cell lines, and the LC50 values of these analogs were indicated over 10 μM. An analog of 9,10-PQ in which the biaryl unit had been deleted displayed a reduced ability to induce tumor cell apoptosis, while the analogs 1,10-phenanthroline-5,6-dione (9) and pyrene-4,5-dione (10), which also had modified biaryl units, exhibited increased tumor cell apoptotic activity. The cis-orthoquinone unit in 9,10-PQ was identified as essential for its ability to induce apoptosis in tumor cells, and its biaryl unit is also considered to influence orthoquinone-mediated apoptotic activity.9,10-Phenanthrenequinone (9,10-PQ) is one of the most abundant quinones among diesel exhaust particulates. Recent data have suggested that quinones induce apoptosis in immune, epithelial and tumor cells, leading to respirator illness; however, the mechanisms by which quinones induce apoptosis and the structure required for this remain unknown. We studied the antitumor activity of 9,10-PQ analogs against two human tumor cell lines, HCT-116 colon tumor cells and HL-60 promyelocytic leukemia cells. The loss of the cis-orthoquinone unit in 9,10-PQ abrogated its ability to induce apoptosis in the two tumor cell lines, and the LC50 values of these analogs were indicated over 10 μM. An analog of 9,10-PQ in which the biaryl unit had been deleted displayed a reduced ability to induce tumor cell apoptosis, while the analogs 1,10-phenanthroline-5,6-dione (9) and pyrene-4,5-dione (10), which also had modified biaryl units, exhibited increased tumor cell apoptotic activity. The cis-orthoquinone unit in 9,10-PQ was identified as essential for its ability to induce apoptosis in tumor cells, and its biaryl unit is also considered to influence orthoquinone-mediated apoptotic activity.

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  • One-pot construction of 3,3'-bisindolylmethanes through Bartoli indole synthesis.

    ( 32 )   20 - 20   2014.12

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    A one-pot approach to 3,3'-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3'-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH4Cl.A one-pot approach to 3,3'-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3'-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH4Cl.

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  • Simple indole alkaloids and those with a non-rearranged monoterpenoid unit.

    ( 32 )   17 - 17   2014.12

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    Covering: 2010-2011. Previous review: Nat. Prod. Rep. 2010, 27, 1630-1680This review covers the literature on simple indole alkaloids and those with a non-rearranged monoterpenoid unit from the beginning of 2010 up to the end of 2011, which includes newly isolated alkaloids, structure determinations, total syntheses and biological activities.Covering: 2010-2011. Previous review: Nat. Prod. Rep. 2010, 27, 1630-1680This review covers the literature on simple indole alkaloids and those with a non-rearranged monoterpenoid unit from the beginning of 2010 up to the end of 2011, which includes newly isolated alkaloids, structure determinations, total syntheses and biological activities.

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  • Calothrixin B誘導体によるHL-60細胞への抗腫瘍活性の発現

    波多江 典之, 西山 卓志, 町支 臣成, 日比野 俐, 阿部 匠, 岡田 知晃, 石倉 稔, 豊田 栄子

    日本薬学会年会要旨集   134年会 ( 2 )   227 - 227   2014.3

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  • Total Synthesis of Antitumor Indole Alkaloids by Cu-catalyzed 6π-electrocyclization

    Abe Takumi, Ishikura Minoru

    Symposium on the Chemistry of Natural Products, symposium papers   56 ( 0 )   Poster4   2014

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    <p> Ellipticine (1), a pyridocarbazole alkaloid with a potent antitumor activity, was isolated from Ochrosia elliptica Labill in 1959. Due to its unique structure as well as potent antitumor activity, 1 have attracted much attention in chemical and biological communities. The structurally-related alkaloids calothrixin A (2) and B (3), a potent antitumor antibiotics, were isolated from cyanobacteria Calothrixin 1999. These alkaloids are characterized by the fused polycyclic ring systems including carbazole. Although there have been reported 6p-electrocyclization that allow concise construction of carbazole core, there was no precedent for construction of carbazoles by catalytic 6p-electrocyclization. We envisaged catalytic 6p-electrocyclization of triene containing indole for the construction of these carbazole core. Herein, we describe the total synthesis of antitumor indole alkaloids based on the Pd-catalyzed tandem cross-coupling/cyclization and Cu-catalyzed 6p-electrocyclization of trienes. </p><p> The triene 6 were readily synthesized from indolylborate 4 and enyne 5 by Pd-catalyzed tandem cross-coupling/cyclization in one-pot protocol. After intensive investigations, we found that (CuOTf)<sub>2</sub>•toluene complexes prompted cyclization of 6 to carbazole 7 in good yields, while other Lewis acids and metal complexes did not cause this cyclization at all. In addition, this Cu-promoted cyclization could proceed in the presence of catalytic amount of (CuOTf)<sub>2</sub>•toluene complexes. This is a first example for 6p-electrocyclization catalyzed by Cu-complexes. Finally, deprotection and oxidation sequeneces of 7 gave ellipticine (1), 9-methoxyellipticine (10), m-alkaloid D (12) and tetrahydroellipticine (13). In the almost same manner, we have completed total synthesis of olivacine (20), guatambuine (22) and janetine (23) as well from carbazole 7d.</p><p> Calothrixin A (2) and B (3) were also synthesized by a convergent methodology that features a concise approach involving the above-mantioned Pd-catalyzed tandem cross-coupling/cyclization, Cu-catalyzed 6p-electrocyclization to construct the carbazole core and Dakin oxidation. In the key Cu-catalyzed 6p-electrocyclization and Dakin oxidation, a combination of Cu(OAc)<sub>2</sub> and PCC turned out to effect conversion of 6b to 26 in one-pot protocol. </p>

    DOI: 10.24496/tennenyuki.56.0_Poster4

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  • タンデムBartoli反応を利用した3,3’-ビスインドリルメタンの簡便合成

    阿部匠, 伊藤智貴, 仲村修平, 石倉稔

    日本薬学会年会要旨集(CD-ROM)   134th   2014

  • ピリドカルバゾールアルカロイドの短工程合成

    阿部匠, 内山章, 池田敏明, 石倉稔

    日本薬学会年会要旨集(CD-ROM)   134th   2014

  • Bartoliインドール合成の新展開:3,3’-ビスインドリルアルカン類のワンポット合成

    阿部匠, 仲村修平, 石倉稔

    複素環化学討論会講演要旨集   44th   2014

  • インドロキナゾリンの簡便合成

    阿部匠, 伊藤智貴, 石倉稔

    反応と合成の進歩シンポジウム講演要旨集   40th   2014

  • Total synthesis of calothrixins A and B by a palladium-catalyzed tandem cyclization / cross-coupling reaction of indolylborate

    ( 31 )   21 - 21   2013.12

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  • Calothrixin B誘導体の合成による抗腫瘍活性の向上

    波多江典之, 阿部匠, 西山卓志, 町支臣成, 日比野俐, 岡田知晃, 石倉稔, 豊田栄子

    メディシナルケミストリーシンポジウム講演要旨集   31st   185   2013.11

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  • 2,2′-ビインドールの触媒的合成法の開発

    阿部匠, 桜田尚季, 村永諒, 柳谷束, 石倉稔

    日本薬学会年会要旨集(CD-ROM)   133rd   2013

  • ビスエリプチシンアルカロイドstrellidimineの合成研究

    石倉稔, 石部祥果, 上田香織, 仲村修平, 阿部匠

    日本薬学会年会要旨集(CD-ROM)   133rd   2013

  • Bartoliインドール合成を経由する3,3’-ビスインドリルメタン類のワンポット合成

    阿部匠, 仲村修平, 柳谷束, 石倉稔

    反応と合成の進歩シンポジウム講演要旨集   39th   2013

  • ビスインドールアルカロイドyuehchukeneの短工程全合成

    石倉稔, 阿部匠

    日本薬学会年会要旨集   132nd ( 2 )   2012

  • ヘキサトリエンのワンポット構築法を利用したCalothrixin類の簡便全合成

    阿部匠, 池田敏明, 石倉稔

    複素環化学討論会講演要旨集   42nd   2012

  • インドリルボレートを用いる抗腫瘍性抗生物質カロトリキシンAとBの全合成

    池田敏明, 阿部匠, 成田忠義, 石倉稔

    日本薬学会年会要旨集   132nd ( 2 )   2012

  • 分子内C-Hアリール化反応を用いる2,2’-ビインドールの触媒的合成

    阿部匠, 桜田尚季, 村永諒, 柳谷束, 石倉稔

    反応と合成の進歩シンポジウム講演要旨集   38th   2012

  • 触媒的1,6-電子環状反応を利用したピリドカルバゾールの合成

    阿部匠, 池田敏明, 石倉稔

    日本薬学会年会要旨集   132nd ( 2 )   2012

  • Total Synthesis of Calothrixins A and B

    Abe Takumi, Ikeda Toshiaki, Ishikura Minoru

    Proceedings of the Symposium on Progress in Organic Reactions and Syntheses   37 ( 0 )   18 - 18   2011

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    We have demonstrated a new approach to synthesizing calothrixins A and B through the palladium-catalyzed tandem cyclization/cross-coupling reaction of indolylborate by taking advantage of the one-pot generation of the hexatrienes as a key intermediate for constructing indolophenanthridine. In addition, the unprecedented use of CuOTf for 6&pi;-electrocyclization of hexatriene was developed. In another key transformation, indolophenanthridine quinone core of calothrixins was prepared from the indolophenanthridine aldehyde <I>via</I> one-pot Dakin oxidation sequence catalyzed by diphenyldiselenide.

    DOI: 10.14895/hannou.37.0.18.0

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  • Calothrixins AとBの全合成

    阿部匠, 池田敏明, 石倉稔

    反応と合成の進歩シンポジウム講演要旨集   37th   2011

  • タンデム型クロスカップリング反応を用いるCalothrixin Bの合成研究

    池田敏明, 阿部匠, 山田康司, 石倉稔

    日本薬学会年会要旨集   131st ( 2 )   2011

  • Indolylcyanocuprateを利用したRhazinilamの合成研究

    阿部匠, 池田敏明, 山田康司, 石倉稔

    日本薬学会年会要旨集   131st ( 2 )   2011

  • 簡便なアゼピノインドール環形成反応を用いたhyrtiazepineの合成研究

    山田康司, 晴山知拓, 阿部匠, 石倉稔

    日本薬学会年会要旨集   131st ( 2 )   2011

  • アゼピノインドールを経由したセロトニン関連化合物の簡便合成法の開発

    山口紗靖佳, 山田康司, 阿部匠, 石倉稔

    日本薬学会年会要旨集   131st ( 2 )   2011

  • Development of Tandem Hydroarylation/Chan-Evans-Lam Coupling Reaction of Bicyclolactam Catalyzed by Combined Metal-Complex

    Abe Takumi, Takeda Hiroyuki, Yamada Koji, Ishikura Minoru

    Proceedings of the Symposium on Progress in Organic Reactions and Syntheses   36 ( 0 )   8 - 8   2010

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    Aryl-substituted 2-azabicyclo[2.2.1]heptanes (aryl-ABH) have significant biological activities. To open the concise entry to aryl-ABH, we have examined metal-catalyzed cross-coupling reaction of arylboronic acids and ABH. When the reaction was carried out with arylboronic acid and ABH in the presence of rhodium/copper combined catalyst under microwave irradiation, diarylated ABH were obtained in one-pot manner. Rhodium complex promoted catalytic addition of arylboronic acids to the double bonds of ABH, and copper complex were essential for the catalytic N-arylation of the amide moiety of ABH.

    DOI: 10.14895/hannou.36.0.8.0

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  • アゼピノインドールを経由したセロトニン関連化合物の簡便合成法

    山口紗靖佳, 山田康司, 阿部匠, 石倉稔

    複素環化学討論会講演要旨集   40th   2010

  • アゼピノインドール類を経由したセロトニン誘導体の合成

    山口紗靖佳, 山田康司, 阿部匠, 石倉稔

    日本薬学会年会要旨集   130th ( 2 )   2010

  • アゼピノインドール型アルカロイドhyrtiazepineの合成研究

    山田康司, 晴山知拓, 阿部匠, 石倉稔

    日本薬学会年会要旨集   130th ( 2 )   2010

  • 銅触媒を用いたRitter型三成分カップリング反応によるN,N’-二置換鎖状アミジンのジアステレオ選択的合成

    阿部匠, 武田浩幸, 山田康司, 石倉稔

    日本薬学会年会要旨集   130th ( 2 )   2010

  • Construction of Azepinoindole nucleus by Reaction of Serotonins with aldehydes in the Presence of a Base

    Haruyama Tomohiro, Yamada Koji, Abe Takumi, Ishikura Minoru

    Proceedings of the Symposium on Progress in Organic Reactions and Syntheses   35 ( 0 )   55 - 55   2009

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    Pictet-Spengler reaction is one of the most versatile synthetic method in heterocyclic synthesis. Generally, tryptamine derivatives are known to react with aldehydes under acidic or neutral conditions to produce beta-calbolines. On the other hand, we have found that the reaction of Nb-benzylserotonin with aldehydes in the presence of a base proceeded the cyclization to the 4-position of the indole ring, producing azepino[5,4,3-cd]indoles. Therefore, we have investigated the applicability of other aldehydes and serotonin derivatives to the cyclization reaction to devise a novel synthetic route to azepinoindole alkaloids.

    DOI: 10.14895/hannou.35.0.55.0

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  • Investigation on the chemical diversity of 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH)

    山口紗靖佳, 武田浩幸, 阿部匠, 山田康司, 石倉稔

    複素環化学討論会講演要旨集   39th   2009

  • Catalytic Diamination of Alkenes with Dichloramine-T and Nitriles as Nitrogen Sources

    Takeda Hiroyuki, Abe Takumi, Yamada koji, Ishikura Minoru

    Proceedings of the Symposium on Progress in Organic Reactions and Syntheses   34 ( 0 )   8 - 8   2008

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    The 1,2-differentiated diamination of unactivated alkenes was achieved using dichloramine-T (TsNCl2 and CH3CN as nitrogen sources in the presence of a catalytic amount of copper(II) complex. Various alkenes and nitriles could be applicable for the diamination, in which the cis-selectivities were observed in all cases. However, a few substrates gave poor yields mainly due to the formation of haloamine side product which would arised from ring-opening of the aziridinium intermediates by Cl- in an SN2 manner instead of CH3CN. In these cases, the enhanced formation of diamine was observed when the reaction was performed at -20 C. The methodology described herein allows rapid access to cis-vicinal diamines.

    DOI: 10.14895/hannou.34.0.8.0

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  • ロジウム錯体を用いる2-アザビシクロ[2.2.1]ヘプト-5-エン-3-オンのアリール化反応の開発

    阿部匠, 高橋有美, 石倉稔

    日本薬学会年会要旨集   128th ( 2 )   2008

  • Synthesis of azepino-indole alkaloids using novel cyclization of serotonin and aldehydes

    晴山知拓, 滑川祐市, 山田康司, 阿部匠, 石倉稔

    複素環化学討論会講演要旨集   38th   2008

  • 銅錯体を用いる2-アザビシクロ[2.2.1]ヘプト-5-エン-3-オンとアリールボロン酸のクロスカップリング反応の開発

    武田浩幸, 阿部匠, 石倉稔

    日本薬学会年会要旨集   128th ( 2 )   2008

  • Development of Catalytic Arylation of Bicyclolactam ABH (2-azabicyclo[2.2.1]hept-5-en-2-one)

    Abe Takumi, Takeda Hiroyuki, Takahashi Yumi, Ishikura Minoru

    Proceedings of the Symposium on Progress in Organic Reactions and Syntheses   33 ( 0 )   54 - 54   2007

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    The arylation of 2-azabicyclo[2.2.1]hept-5-en-3-ones (ABH) with arylboronic acids was achieved using a catalytic amount of a rhodium(I) complex under microwave irradiation, in which the ring-opening of ABH and the multiple alkylation did not occur. The remote substituents effects on the chemical yields and the regioselectivities (syn : anti = 56 : 44 to 85 : 15) were observed. On the other hand, the reaction under the conventional conditions was sluggish in all cases. Using copper(II) complex, addition of arylboronic acids to N-H ABH under the conventional conditions afforded N-arylated ABH in good yield. In this case, the microwave irradiation was also found to promote the arylation of ABH, improving the rates and yields of these reactions.

    DOI: 10.14895/hannou.33.0.54.0

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  • Synthetic study of 2-alkoxyindoles

    山田康司, 小坂祐太, 武田浩幸, 阿部匠, 石倉稔

    複素環化学討論会講演要旨集   37th   2007

  • Enantioselective Amidation of Silyl Enol Ether Catalyzed by Chiral Dirhodium(II) Complexes

    Tanaka Masahiko, Abe Takumi, Anada Masahiro, Hashimoto Shunichi

    Proceedings of the Symposium on Progress in Organic Reactions and Syntheses   32 ( 0 )   28 - 28   2006

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    Language:Japanese   Publisher:Division of Organic Chemistry, The Pharmaceutical Society of Japan  

    A recent study from our laboratory has shown that Rh2(S-TCPTTL)4, characterized by substitution of chlorine atoms for four hydrogen atoms on the phthalimido group in the parent Rh(II) complex, is well suited for enantioselective C&ndash;H amidation reation with [(4-nitrophenyl)sulfonylimino]phenyliodinane. As a logical extension of our study in this area, we addressed the enantioselective amidation of silyl enol ethers catalyzed by chiral Rh(II) carboxylates. The Rh(II)-catalyzed aziridination of acyclic silyl enol ethers with [(2-nitrophenyl)sulfonylimino]phenyliodinane followed by treatment with aq. TFA afforded optically active &alpha;-amino ketones. The fluorinated catalyst, Rh2(S-TFPTTL)4, proved to be the catalyst of choice for this process, exhibiting the highest enantioselectivity of 95% ee. The effectiveness of the present catalytic method has been demonstrated by the enantioselective synthesis of (&ndash;)-metazocine.

    DOI: 10.14895/hannou.32.0.28.0

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  • 高性能スピロ型ジホスファイト配位子の開発

    阿部匠, 日下奈津子, 穴田仁洋, 橋本俊一

    日本薬学会年会要旨集   126th ( 4 )   2006

  • スピロ型ジホスファイト配位子の開発と不斉触媒反応への応用

    阿部匠, 日下奈津子, 穴田仁洋, 橋本俊一

    次世代を担う有機化学シンポジウム講演要旨集   4th   2006

  • キラルなRh(II)錯体を用いたα-アルキル-α-ジアゾアセタートの分子内不斉C-H挿入反応

    南和志, 小野塚智洋, 阿部匠, 穴田仁洋, 橋本俊一

    日本薬学会年会要旨集   126th ( 4 )   2006

  • 新規スピロ型ジホスファイト配位子-ロジウム錯体を触媒とする有機ボロン酸の不斉共役付加反応

    阿部匠, 日下奈津子, 穴田仁洋, 橋本俊一

    日本薬学会年会要旨集   125th ( 4 )   2005

  • 新規スピロ型ジホスファイト配位子を用いた触媒的不斉アリル化反応

    阿部匠, 大石寛之, 田村雅史, 穴田仁洋, 橋本俊一

    日本薬学会年会要旨集   123rd ( 2 )   2003

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Awards

  • Outstanding Reviewer Royal Society of Chemistry (英国王立化学会)

    2023.3   RSC Advances (RSC Adv.)  

    阿部匠

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  • 岡山工学振興会科学技術賞

    2022.7   公益財団法人 岡山工学振興会  

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  • Outstanding Reviewer Royal Society of Chemistry (英国王立化学会)

    2022.3   Organic Biomolecular Chemistry (OBC)  

    阿部匠

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  • アステラス製薬研究企画賞

    2014.12   有機合成化学協会   「金属錯体のエージングを利用した新規反応の開発」

    阿部匠

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  • 奨励賞

    2011.11   日本薬学会北海道支部   「多官能性合成素子の開発と天然物合成への応用」

    阿部匠

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Research Projects

  • インドールの極性転換を利用した新規感染症治療薬の創出

    2023.04 - 2024.03

    公益財団法人 高橋産業経済研究財団  研究助成(継続) 

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  • 酸化還元制御型第四級炭素構築法の開発

    2023.04 - 2024.03

    公益財団法人 中部電気利用基礎研究振興財団  研究助成A2 

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  • アミノインドール合成法を基盤とした新規感染症治療薬の創出

    2022.06 - 2023.03

    公益財団法人 岡山工学振興会  一般研究助成  一般研究助成

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  • 薬剤耐性ガン治療薬の創出を指向したα置換インドリルアセタミド誘導体の網羅的合成

    2022.04 - 2027.03

    公益財団法人 武田科学振興財団  薬学系研究助成 

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  • アルコキシ基を極性転換スイッチとした分子変換手法の開発

    Grant number:22K06503  2022.04 - 2025.03

    日本学術振興会  科学研究費補助金 基盤研究(C)  基盤研究(C)

    阿部 匠

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    Authorship:Principal investigator 

    Grant amount:\4160000 ( Direct expense: \3200000 、 Indirect expense:\960000 )

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  • インドールの極性転換を利用した新規感染症治療薬の創出

    2022.04 - 2023.03

    公益財団法人 高橋産業経済研究財団  研究助成 

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  • Development of Reactivity of Aging Metal-Complexes

    Grant number:16K18849  2016.04 - 2020.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Young Scientists (B)  Grant-in-Aid for Young Scientists (B)

    ABE Takumi

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    Grant amount:\4160000 ( Direct expense: \3200000 、 Indirect expense:\960000 )

    Investigation of the reactivity of aging metal complexes are important in the green chemistry due to their high cost. This works were conducted from viewpoint of both use of aging metal complexes and development of novel reactivity of the aging metal complexes. It is found that aged Lewis acid catalyst could promote dehydrate Mannnichi-type cyclization of 2-hydroxyindolines. Thus the aged Lewis acid showed higher reactivity in comparison with fresh Lewis acid. We accomplished the total synthesis of iheyamine A using this aged Lewis acid catalyst.

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  • アレルギー皮膚疾患患者に用いることのできる優しい新規染料の合成探索

    2016.04 - 2017.03

    一般財団法人ホーユー科学財団  研究助成 

    阿部匠

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    Authorship:Principal investigator  Grant type:Competitive

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  • 心筋様細胞への分化促進剤の設計と合成探索

    2015.07

    一般財団法人北海道心臓協会  研究開発調査助成 

    阿部匠

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    Authorship:Principal investigator  Grant type:Competitive

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  • トリエンの銅触媒カルボ6p-電子環状反応を用いる縮環型カルバゾールの合成

    2015.06 - 2016.03

    公益財団法人秋山記念生命科学振興財団  研究助成(奨励) 

    阿部匠

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    Authorship:Principal investigator  Grant type:Competitive

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  • ビスインドリルメタンの新規合成

    2015.06

    公益財団法人伊藤医薬学術交流財団  海外留学研究等の交流助成 

    阿部匠

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    Authorship:Principal investigator  Grant type:Competitive

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  • 金属錯体のエージングを利用した新規反応の開発

    2015.04 - 2017.03

    アステラス製薬  有機合成化学協会研究企画賞 

    阿部匠

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    Authorship:Principal investigator  Grant type:Competitive

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  • Synthesis of bioactive indole alkaloid using functionallised synthetic synthon

    Grant number:26460012  2014.04 - 2017.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

    Ishikura Minoru

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    Grant amount:\5070000 ( Direct expense: \3900000 、 Indirect expense:\1170000 )

    Cross-coupling reaction of indolylborate was used for concise total syntheses of pyrido[4,3-b]carbazole alkaloids. Unprecedented use of copper(I) triflate toluene complex for electrocyclization of hexatriene intermediate successfully improved the construction of pyridocarbazoles. Evaluation of synthetic alkaloids against HCT-116 and HL-60 cell lines was carried out. Concise syntheses of indoloquinazoline alkaloids were developed. Oxidative dimerization of indole-3-carbaldehyde provided tryptanthrin in a one-pot. Further transformation of tryptanthrin through Baeyer-Villiger oxidation provided cephalanthrin A. Oxidative coupling between indole-3-carboxylate and isatoic anhydride provided phaitanthrin E.

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  • Development of novel synthetic method and its use for synthesis of natural products

    Grant number:22590010  2010 - 2012

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

    ISHIKURA Minoru, YAMADA Koji, ABE Takumi

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    Grant amount:\4680000 ( Direct expense: \3600000 、 Indirect expense:\1080000 )

    Cross-coupling reaction of indolylborate was used for concise total synththesis of calothrixins A and B. Unprecedented use of CuOTf for 6π-electrocyclization was also found, which was successfully applied for the improved synthesis of ellipticine. Introduction of aryl substituents to bicyclic lactam ABH was performed by metal-catalyzed coupling process.

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  • Development of multi-functionalized synthon for the synthesis of bioactive natural products

    Grant number:18590011  2006 - 2008

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

    ISHIKURA Minoru

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    Grant amount:\4020000 ( Direct expense: \3600000 、 Indirect expense:\420000 )

    多機能な化学反応性を有する合成中間体を基盤とする合成法を開発することは、多様な化学構造を有する生理活性物質の合成を行ううえで有用な方法論となる。本研究では、インドリルボレートとビシクロラクタムであるABHの合成中間体としての有用性に着目し、その応用性の開発をすすめた。この結果、重要な生理活性をもつインドールアルカロイド(tubifoline, olivacine)の新規合成法を開発できた。また、中枢および末梢神経に対して強い生理作用を持つABH誘導体の直接的合成法を開発できた。

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