Faculty Profiles - ABE Takumi

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

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

It was shown that dichloramine-T (1) reacted with cyclohexene in acetonitrile to give N'-(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

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

Language：English Publisher：ROYAL SOC CHEMISTRY

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

J-GLOBAL

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

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

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

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

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

[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.

DOI： 10.1021/o1702019b

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

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

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.

DOI： 10.3987/COM-07-S(K)63

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

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

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.

DOI： 10.1002/adsc.200600591

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

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

Language：English Publishing type：Research paper (scientific journal) Publisher：PHARMACEUTICAL SOC JAPAN

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.

DOI： 10.1248/cpb.53.1366

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