研究者詳細 - 坂倉　彰

論文 - 坂倉　彰

分割表示 103 件中 1 - 20 件目／全件表示 >>

Rapid construction of a diterpene-inspired tetracyclic skeleton bearing bicyclo[3.2.1]octane rings based on desymmetrization of 1,3-diketones

Hidetoshi Kamada, Haruki Mizoguchi, Akira Sakakura

Tetrahedron Letters 2025年2月

Synthesis and biological evaluation of coprinoferrin, an acylated tripeptide hydroxamate siderophore

Ichiro Hayakawa, Tomoki Isogai, Jun Takanishi, Shihori Asai, Chika Ando, Tomohiro Tsutsumi, Kenji Watanabe, Akira Sakakura, Yuta Tsunematsu

Organic & Biomolecular Chemistry 2024年

掲載種別：研究論文（学術雑誌）出版者・発行元：Royal Society of Chemistry (RSC)

Coprinoferrin (CPF), originally isolated from a genetically engineered strain (∆laeA) of mushroom fungus Coprinopsis cinerea, is an acylated tripeptide hydroxamate consisting of tandem aligned N5-hexanoyl-N5-hydroxy-L-ornithine with modifications of N-acetyl and...

DOI： 10.1039/d3ob01850d

researchmap

Visible-Light-Photoexcited Palladium-Catalyzed Silylmethylation of Benzyl Alcohol Derivatives 招待査読

Haruki Mizoguchi, Akira Sakakura, Ryuji Yoshida, Haruka Ikeda

Synlett 34 ( 20 ) 2451 - 2454 2023年7月

Enantioselective construction of beta-hydroxy-alpha,alpha-disubstituted alpha-amino acid derivatives via direct aldol reaction of alpha-imino esters 査読

Yuya Araki, Masato Hanada, Yoshiko Iguchi, Haruki Mizoguchi, Akira Sakakura

TETRAHEDRON 110 2022年3月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

The beta-hydroxy-alpha,alpha-disubstituted alpha-amino acid is a valuable structural motif for research in the field of bioorganic chemistry and in the development of peptide drugs. This report describes the enantioselective direct-aldol reaction of alpha-imino esters with glyoxylate esters. We discovered that a catalytic amount of Co(OAc)(2)-pybox complex catalyzed the aldol reaction of salicylaldehyde-derived alpha-imino esters with benzyl glyoxylate in good yield and enantioselectivity. In addition, hydrolysis of the imine moiety of the aldol products followed by Boc protection of the resultant amino group gave the N-Boc-protected amino acid derivatives. (C) 2022 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2022.132695

Web of Science

researchmap

Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement 査読

Haruki Mizoguchi, Hidetoshi Kamada, Kazuki Morimoto, Ryuji Yoshida, Akira Sakakura

Chemical Science 13 ( 33 ) 9580 - 9585 2022年

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Royal Society of Chemistry ({RSC})

A stereoselective annulative coupling of a vinylboronic ester ate-complex with arynes producing cyclic borinic esters has been developed. An annulation reaction that proceeded through the formation of two C-C bonds and a C-B bond was realized by exploiting a 1,2-metallate rearrangement of boronate triggered by the addition of a vinyl group to the strained triple bond of an aryne. The generated aryl anion would then cyclize to a boron atom to complete the annulation cascade. The annulated borinic ester could be converted to boronic acids and their derivatives by oxidation, halogenation, and cross-coupling. Particularly, halogenation and Suzuki-Miyaura coupling proceeded in a site-selective fashion and produced highly substituted alkylboronic acid derivatives.

DOI： 10.1039/D2SC02623F

Web of Science

researchmap

Toward the Synthesis of Paspaline-Type Indole-Terpenes: Stereoselective Construction of Core Scaffold with Contiguous Asymmetric Quaternary Carbon Centers 査読

Ichiro Hayakawa, Naochika Matsumaru, Akira Sakakura

The Journal of Organic Chemistry 86 ( 14 ) 9802 - 9810 2021年7月

Strain-release Difunctionalization of C–C σ- and π-bonds of an Organoboron Ate-complex through 1,2-Metallate Rearrangement 招待査読

Haruki Mizoguchi, Akira Sakakura

Chemistry Letters 50 ( 4 ) 792 - 799 2021年4月

Dual Inhibition of γ-Tubulin and Plk1 Induces Mitotic Cell Death 査読

Haruna Ebisu, Kana Shintani, Takumi Chinen, Yoko Nagumo, Shuya Shioda, Taisei Hatanaka, Akira Sakakura, Ichiro Hayakawa, Hideo Kigoshi, Takeo Usui

Frontiers in Pharmacology 11 2021年1月

掲載種別：研究論文（学術雑誌）出版者・発行元：Frontiers Media SA

α/β-Tubulin inhibitors that alter microtubule (MT) dynamics are commonly used in cancer therapy, however, these inhibitors also cause severe side effects such as peripheral neuropathy. γ-Tubulin is a possible target as antitumor drugs with low side effects, but the antitumor effect of γ-tubulin inhibitors has not been reported yet. In this study, we verified the antitumor activity of gatastatin, a γ-tubulin specific inhibitor. The cytotoxicity of gatastatin was relatively weak compared with that of the conventional MT inhibitors, paclitaxel and vinblastine. To improve the cytotoxicity, we screened the chemicals that improve the effects of gatastatin and found that BI 2536, a Plk1 inhibitor, greatly increases the cytotoxicity of gatastatin. Co-treatment with gatastatin and BI 2536 arrested cell cycle progression at mitosis with abnormal spindles. Moreover, mitotic cell death induced by the combined treatment was suppressed by the Mps1 inhibitor, reversine. These findings suggest that co-treatment with Plk1 and γ-tubulin inhibitors causes spindle assembly checkpoint-dependent mitotic cell death by impairing centrosome functions. These results raise the possibility of Plk1 and γ-tubulin inhibitor co-treatment as a novel cancer chemotherapy.

DOI： 10.3389/fphar.2020.620185

researchmap

Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester–Amide Exchange Reaction 査読

Akira Sakakura, Ryota Nakao, Yudai Fujii, Ichiro Hayakawa, Haruki Mizoguchi

Synlett 31 ( 20 ) 2018 - 2022 2020年12月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Georg Thieme Verlag {KG}

<title>Abstract</title>
C
1-Symmetric chiral ammonium salt catalysts induced a kinetic resolution of racemic α-nitrolactones through an asymmetric ester–amide exchange reaction. The corresponding amides were obtained with high enantioselectivities and high S (= k
fast/k
slow) values. This reaction system is a useful approach for obtaining carbocyclic quaternary α-nitroamides as chiral building blocks.

DOI： 10.1055/s-0040-1707303

researchmap

Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts 査読

Akira Sakakura, Yudai Fujii, Ryota Nakao, Saki Sugihara, Keita Fujita, Yuya Araki, Takayuki Kudoh, Ichiro Hayakawa, Haruki Mizoguchi

Synlett 31 ( 20 ) 2013 - 2017 2020年12月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Georg Thieme Verlag {KG}

<title>Abstract</title>An enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C
1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

DOI： 10.1055/s-0040-1707302

researchmap

Structure Optimization of Gatastatin for the Development of gamma-Tubulin-Specific Inhibitor 査読

Kana Shintani, Haruna Ebisu, Minagi Mukaiyama, Taisei Hatanaka, Takumi Chinen, Daisuke Takao, Yoko Nagumo, Akira Sakakura, Ichiro Hayakawa, Takeo Usui

ACS MEDICINAL CHEMISTRY LETTERS 11 ( 6 ) 1125 - 1129 2020年6月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER CHEMICAL SOC

Gatastatin (O-7-benzyl glaziovianin A) is a gamma-tubulin-specific inhibitor that is used to investigate gamma-tubulin function in cells. We have previously reported that the unsubstituted phenyl ring of the O-7-benzyl group in gatastatin is important for gamma-tubulin inhibition. To obtain further structural information regarding gamma-tubulin inhibition, we synthesized several gatastatin derivatives containing a fixed O-7-benzyl moiety. Modifications of the B-ring resulted in drastic decrease in cytotoxicity, abnormal spindle formation activity, and inhibition of microtubule (MT) nucleation. In contrast, various O-6-alkylated gatastatin derivatives showed potent cytotoxicity, induced abnormal spindle formation, and inhibited MT nucleation. We had previously reported that O-6-benzyl glaziovianin A is a potent alpha/beta-tubulin inhibitor; thus, these new results suggest that the O-6-position restricts affinity for alpha/beta- and gamma-tubulin. Considering that an O-7-benzyl group increases specificity for gamma-tubulin, more potent and specific gamma-tubulin inhibitors can be generated through O-6-modifications of gatastatin.

DOI： 10.1021/acsmedchemlett.9b00526

Web of Science

researchmap

Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction 査読

Yuya Araki, Natsumi Miyoshi, Kazuki Morimoto, Takayuki Kudoh, Haruki Mizoguchi, Akira Sakakura

JOURNAL OF ORGANIC CHEMISTRY 85 ( 2 ) 798 - 805 2020年1月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER CHEMICAL SOC

A formal total synthesis of manzacidin B is described. beta,beta-Disubstituted gamma-hydroxy-beta-aminoalcohol, the key structure of manzacidin B, is stereoselectively constructed via sequential Henry reactions. By taking advantage of noncovalent interactions, such as intramolecular hydrogen bonding and chelation, we could diastereodivergently control the stereoselectivity of the Henry reaction.

DOI： 10.1021/acs.joc.9b02811

Web of Science

researchmap

Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate 査読

Haruki Mizoguchi, Masaya Seriu, Akira Sakakura

Chemical Communications 56 ( 99 ) 15545 - 15548 2020年

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Royal Society of Chemistry (RSC)

A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed.

DOI： 10.1039/d0cc07134j

Web of Science

researchmap

Toward the Synthesis of SB-203207: Construction of Four Contiguous Nitrogen-Containing Stereogenic Centers 査読

Ichiro Hayakawa, Anna Nagayasu, Akira Sakakura

The Journal of Organic Chemistry 84 ( 23 ) 15614 - 15623 2019年12月

Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts 査読

Chihiro Kidou, Haruki Mizoguchi, Tatsuo Nehira, Akira Sakakura

Synlett 30 ( 15 ) 1835 - 1839 2019年9月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Georg Thieme Verlag {KG}

Organoammonium salts of dipeptide-derived chiral triamines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of α-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although α-(p-methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, α-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.

DOI： 10.1055/s-0039-1690133

Web of Science

researchmap

Toward the Synthesis of Yuzurimine-Type Alkaloids: Stereoselective Construction of the Heterocyclic Portions of Deoxyyuzurimine and Macrodaphnine 査読国際誌

Ichiro Hayakawa, Ryosuke Nagatani, Masaki Ikeda, Dong-eun Yoo, Keita Saito, Hideo Kigoshi, Akira Sakakura

Organic Letters 21 ( 16 ) 6337 - 6341 2019年8月

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

The heterocyclic portions of yuzurimine-type alkaloids, such as deoxyyuzurimine and macrodaphnine, were synthesized by using a stereoselective hydroboration-oxidation reaction to install the C20 methyl group, the intramolecular Mitsunobu reaction to construct the E-ring portion, and the intramolecular SN2 reaction to construct the F-ring portion as key steps.

DOI： 10.1021/acs.orglett.9b02232

Web of Science

PubMed

researchmap

Thioureas as Highly Active Catalysts for Biomimetic Bromocyclization of Geranyl Derivatives 査読

Miyuki Terazaki, Kei-ichi Shiomoto, Haruki Mizoguchi, Akira Sakakura

Organic Letters 21 ( 7 ) 2073 - 2076 2019年4月

Catalytic enantioselective Hosomi–Sakurai reaction of α-ketoesters promoted by chiral copper(ii) complexes 査読

Yutaro Niwa, Mayu Miyake, Ichiro Hayakawa, Akira Sakakura

Chemical Communications 55 ( 27 ) 3923 - 3926 2019年

担当区分：最終著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Royal Society of Chemistry ({RSC})

The first catalytic enantioselective Hosomi−Sakurai reaction of α-ketoesters.

DOI： 10.1039/C9CC01159E

Web of Science

researchmap

Chiral Pyrophosphoric Acid Catalysts for the para-Selective and Enantioselective Aza-Friedel–Crafts Reaction of Phenols 査読

Akira Sakakura, Manabu Hatano, Kazuaki Ishihara, Haruka Okamoto, Kohei Toh, Takuya Mochizuki, Hidefumi Nakatsuji

Synthesis 50 ( 23 ) 4577 - 4590 2018年12月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Georg Thieme Verlag {KG}

Chiral BINOL-derived pyrophosphoric acid catalysts were developed and used for the regio- and enantioselective aza-Friedel–Crafts reaction of phenols with aldimines. ortho/para-Directing phenols could react at the para-position selectively with moderate to good enantioselectivities. Moreover, the gram-scale transformation of a product into the key intermediate for the antifungal agent (R)-bifonazole was demonstrated.

DOI： 10.1055/s-0037-1610250

Web of Science

researchmap

Enantioselective aza-Friedel–Crafts reaction of furan with α-ketimino esters induced by a conjugated double hydrogen bond network of chiral bis(phosphoric acid) catalysts 査読

Manabu Hatano, Haruka Okamoto, Taro Kawakami, Kohei Toh, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara

Chemical Science 9 ( 30 ) 6361 - 6367 2018年

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Royal Society of Chemistry ({RSC})

Chiral <italic>C</italic>₂- and <italic>C</italic>₁-symmetric BINOL-derived bis(phosphoric acid) catalysts facilitated the enantioselective aza-Friedel–Crafts reaction of 2-methoxyfuran with α-ketimino esters.

DOI： 10.1039/C8SC02290A

Web of Science

researchmap

　前のページ - 次のページ　

<坂倉 彰>

論文 - 坂倉 彰

<坂倉　彰>

論文 - 坂倉　彰