研究者詳細 - 好光　健彦

MISC - 好光　健彦

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Studies of the Asymmetric Total Synthesis of Clavilactone D by the 'Lariat' Cyclization Strategy

Takehiko Yoshimitsu, Shoji Nojima, Masashi Hashimoto, Koji Tsukamoto, Tetsuaki Tanaka

SYNTHESIS-STUTTGART 17 ( 17 ) 2963 - 2969 2009年9月

記述言語：英語出版者・発行元：GEORG THIEME VERLAG KG

A route to the core structure of clavilactone D, a new member of the tyrosine kinase inhibitors, is reported. The route employs sequential cyclization initiated by iodo etherification followed by Friedel-Crafts cyclization to furnish a polycyclic lactone fused with an aromatic ring, which is readily transformed into the proposed clavilactone scaffold.

DOI： 10.1055/s-0029-1216909

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Total Synthesis of the β-Catenin Inhibitor, (－)-Agelastatin A: A Second-Generation Approach Based on Radical Aminobromination

T.Yoshimitsu, T. Ino, N. Futamura, T. Kamon, T. Tanaka

Org. Lett. 11 ( 15 ) 3402 - 3405 2009年8月

SYNTHESIS OF CHAETOMELLIC ANHYDRIDE A, A POTENT INHIBITOR OF RAS PROTEIN FARNESYLTRANSFERASE

Takehiko Yoshimitsu, Yoshimasa Arano, Tomohiro Kaji, Tatsunori Ino, Hiroto Nagaoka, Tetsuaki Tanaka

HETEROCYCLES 77 ( 1 ) 179 - 186 2009年1月

記述言語：英語出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

Chaetomellic anhydride A, a potent inhibitor of Ras protein farnesyltransferase, was synthesized in 61% yield over four steps from methyl propionate. The synthesis features palladium-catalyzed carboxylation reaction under Cacchi conditions, efficiently incorporating carbon monoxide generated in situ from acetic formic anhydride into beta-carbomethoxyalkenyl triflate, and giving rise to the maleic anhydride motif of chaetomellic anhydride A. Noteworthy is the remarkable reactivity of the carboxylation reaction that takes place at room temperature despite the fact that common palladium-catalyzed carboxylations generally require rather harsh conditions. The scope of the method is also presented.

DOI： 10.3987/COM-08-S(F)16

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Enantiocontrolled Synthesis of Polychlorinated Hydrocarbon Motifs: A Nucleophilic Multiple Chlorination Process Revisited

Takehiko Yoshimitsu, Naoya Fukumoto, Tetsuaki Tanaka

JOURNAL OF ORGANIC CHEMISTRY 74 ( 2 ) 696 - 702 2009年1月

記述言語：英語出版者・発行元：AMER CHEMICAL SOC

Polychlorinated hydrocarbon motifs have been synthesized in enantiomerically pure forms by means of nucleophilic multiple chlorinations of chiral epoxides, which stereospecifically incorporate halogen atoms into oxygenated molecular scaffolds. The present study demonstrates the scope of the N-chlorosuccinimide (NCS)/organophosphine reagent system that forms multiple sp(3)C-Cl bonds in a regularly repeating pattern, with proper stereochemical configurations and evaluates its applicability to various epoxides having elaborate structures. It is noteworthy that tetrachlorinated motifs are produced in one step from bisepoxides by using NCS/Ph(3)P. Furthermore, Ph(2)PCl used in combination with NCS has been found to serve as a potentially useful alternative to NCS/Ph(3)P, especially for promoting dichlorination reactions of alkenyl-substituted epoxides.

DOI： 10.1021/jo802093d

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Total Synthesis of (-)-Agelastatin A

Takehiko Yoshimitsu, Tatsunori Ino, Tetsuaki Tanaka

ORGANIC LETTERS 10 ( 23 ) 5457 - 5460 2008年12月

記述言語：英語出版者・発行元：AMER CHEMICAL SOC

A new route to (-)-agelastatin A is reported. The requisite nitrogen functionalities of the agelastatin core have been installed by intramolecular aziridination of an azidoformate and subsequent regioselective azidation, leading to net trans-diamination of the double bond. The present synthesis also demonstrates two new protocols for the preparation of an imidazolidinone hemiaminal motif from an oxazolidinone intermediate which comprise sequential N-tert-butoxycarbonylation, urea formation, hydrolysis, and oxidative cyclization, and direct aminolysis and subsequent oxidative cyclization.

DOI： 10.1021/ol802225g

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Synthesis of (±)-Aphanorphine: a New Approach to Tricyclic 3-Benzazepine Scaffold Using Two Radical C-C Bond-Forming Reactions

Yoshimitsu, T, Atsumi, C, Iimori, E, Nagaoka, H, Tanaka, T

Tetrahedron Lett. 49 ( 29-30 ) 4473 - 4475 2008年7月

フリーラジカルが拓くヘテロ分子骨格形成の新手法

好光健彦, 田中徹明

生産と技術 90 ( 1 ) 99 - 101 2008年

Radical fixation of functionalized carbon resources: alpha-sp(3)C-H carbamoylation of tertiary amines with aryl isocyanates

Takehiko Yoshimitsu, Kenichi Matsuda, Hiroto Nagaoka, Koji Tsukamoto, Tetsuaki Tanaka

ORGANIC LETTERS 9 ( 24 ) 5115 - 5118 2007年11月

記述言語：英語出版者・発行元：AMER CHEMICAL SOC

A new carbamoylation of tertiary amines is reported. This rare C-H transformation features the direct generation of alpha-aminoalkyl radicals from tertiary amines, followed by the addition of the resultant nucleophilic radicals to isocyanates, enabling unique access to N,N-dlalkylated amino acid derivatives. The authors put forward a mechanistic proposal that is based on the isolation of borinamides produced by capturing nitrogen radical intermediates with Et3B. The present transformation provides a novel one-step process for producing mepivacaine, a clinically important local anesthetic, from readily available materials.

DOI： 10.1021/ol7023295

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フリーラジカルによるα-ヘテロ原子置換sp3炭素―水素結合の新変換法の発見と進展

好光健彦

ファルマシア‐最前線‐ 43 ( 3 ) 219 - 223 2007年

高反応性ラジカル種が誘起する炭素-炭素および炭素-水素結合変換と生物活性物質合成への活用

好光健彦, 長岡博人, 田中徹明

有機合成化学協会誌 65 665 - 676 2007年

解説「Barton反応」

好光健彦

有機合成化学協会誌 65 727 - 727 2007年

現代化学増刊43 最新有機合成化学ヘテロ原子・遷移金属化合物を用いる合成, 奈良坂紘一,岩澤伸治編, 東京化学同人, B5, 220頁, 4,410円

好光健彦

ファルマシア 41 ( 8 ) 740 - 740 2005年8月

Radical hydroxyalkylation of C-H bond adjacent to nitrogen of tertiary amides, ureas, and amines

T Yoshimitsu, Y Arano, H Nagaoka

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 127 ( 33 ) 11610 - 11611 2005年8月

Radical alpha-C-H hydroxyalkylation of ethers and acetal

T Yoshimitsu, Y Arano, H Nagaoka

JOURNAL OF ORGANIC CHEMISTRY 70 ( 6 ) 2342 - 2345 2005年3月

Studies on the total synthesis of (-)-CP-263,114

T Yoshimitsu, S Sasaki, Y Arano, H Nagaoka

JOURNAL OF ORGANIC CHEMISTRY 69 ( 26 ) 9262 - 9268 2004年12月

記述言語：英語掲載種別：書評論文，書評，文献紹介等出版者・発行元：AMER CHEMICAL SOC

Alkoxyl radicals have a wide range of applications in organic synthesis due to their remarkable chemical properties in molecular transformation. The present study shows two types of alkoxyl radicals (primary vs tertiary) to selectively undergo dehydrogenation and beta-scission to give rise to key structural elements of (-)-CP-263,114 (1). By alkoxyl radical transformation followed by installation of the C19-C25 (CP numbering) side chain and the bridged bisacetal unit, the functionalized CP precursor 2 was obtained.

DOI： 10.1021/jo048681u

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Total synthesis of (+)-muconin

T Yoshimitsu, T Makino, H Nagaoka

JOURNAL OF ORGANIC CHEMISTRY 69 ( 6 ) 1993 - 1998 2004年3月

記述言語：英語出版者・発行元：AMER CHEMICAL SOC

(+)-Muconin (1), isolated from the leaves of Rollinia mucosa (Jacq.) Baill. (Annonaceae), is a sequential THF/THP-possessing acetogenin that exhibits potent and selective in vitro cytotoxicity toward pancreatic and breast tumor cell lines. In this study, a new route was established for obtaining (+)-muconin (1) starting with (-)-muricatacin (2), a compound recently synthesized via the novel alpha-C-H hydroxyalkylation and alpha'-C-H oxidation of tetrahydrofuran.

DOI： 10.1021/jo0303721

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Synthesis of (-)-muricatacin via alpha- and alpha '-C-H bond functionalization of tetrahydrofuran

T Yoshimitsu, T Makino, H Nagaoka

JOURNAL OF ORGANIC CHEMISTRY 68 ( 19 ) 7548 - 7550 2003年9月

記述言語：英語出版者・発行元：AMER CHEMICAL SOC

(-)-Muricatacin, a potent cytotoxic (4R,5R)-5-hydroxyheptadecan-4-olide, has been synthesized through alpha-C-H hydroxyalkylation and alpha'-C-H oxidation of tetrahydrofaran. This study presents a novel method for C-H bond functionalization as a means for preparing gamma-(hydroxyalkyl)-gamma-butyrolactones.

DOI： 10.1021/jo0301696

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Hydroxyalkylation of alpha-C-H bonds of tetrahydrofuran with aldehydes in the presence of triethylborane and tert-butyl hydroperoxide

T Yoshimitsu, Y Arano, H Nagaoka

JOURNAL OF ORGANIC CHEMISTRY 68 ( 2 ) 625 - 627 2003年1月

記述言語：英語出版者・発行元：AMER CHEMICAL SOC

The alpha-hydroxyalkylation of tetrahydrofuran with aldehydes via radical C-H abstraction was conducted using triethylborane in the presence of tert-butyl hydroperoxide. This study presents a rare instance of direct intermolecular radical addition of unactivated cyclic ether to aldehydes.

DOI： 10.1021/jo020590e

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Synthesis of the CD ring system of paclitaxel by atom-transfer radical annulation reaction

T Yoshimitsu, H Nakajima, H Nagaoka

TETRAHEDRON LETTERS 43 ( 47 ) 8587 - 8590 2002年11月

Asymmetric synthesis of the core structure of (-)-CP-263,114

T Yoshimitsu, S Yanagisawa, H Nagaoka

ORGANIC LETTERS 2 ( 23 ) 3751 - 3754 2000年11月

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