Faculty Profiles - ABE Takumi

Papers - ABE Takumi

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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

Language：English Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

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.

DOI： 10.1002/ejoc.201600246

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

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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.

DOI： 10.3987/COM-15-S(T)5

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

Authorship：Lead author Language：Japanese Publisher：Society of Synthetic Organic Chemistry

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.

DOI： 10.5059/yukigoseikyokaishi.74.117

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

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

Takumi Abe, Minoru Ishikura

HETEROCYCLES 90 ( 1 ) 673 - 680 2015.1

Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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

DOI： 10.3987/COM-14-S(K)28

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

Language：English Publisher：ROYAL SOC CHEMISTRY

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.

DOI： 10.1039/c5np00032g

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

Language：English Publishing type：Research paper (scientific journal) Publisher：SPRINGER BIRKHAUSER

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.

DOI： 10.1007/s00044-014-1061-6

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

Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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.

DOI： 10.1016/j.tetlet.2014.07.113

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

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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.

DOI： 10.1016/j.tet.2014.01.015

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

Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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

DOI： 10.3987/COM-13-S(S)31

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

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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.

DOI： 10.1016/j.bmcl.2013.06.015

Biomimetic transamination of α-keto esters Reviewed

Takumi Abe

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

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

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.

DOI： 10.5059/yukigoseikyokaishi.71.62

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

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

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.

DOI： 10.1021/ol401486s

Synthesis of indole compounds using multifunctional synthons Reviewed

Takumi Abe

Yakugaku Zasshi 133 ( 1 ) 99 - 106 2013

Authorship：Lead author,　Last author,　Corresponding author Language：Japanese Publisher：日本薬学会

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.

DOI： 10.1248/yakushi.12-00233

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

Language：English Publisher：ROYAL SOC CHEMISTRY

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.

DOI： 10.1039/c3np20118j

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

Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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.

DOI： 10.3987/COM-12-S(N)49

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

Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

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

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

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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.

DOI： 10.1016/j.bmcl.2012.05.064

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

Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

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.

DOI： 10.1021/ol201107a

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

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

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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