Total synthesis and determination of the absolute configuration of (-)-idesolide

Hiroyuki Yamakoshi; Masatoshi Shibuya; Masaki Tomizawa; Yuji Osada; Naoki Kanoh; Yoshiharu Iwabuchi

doi:10.1021/ol9029676

Total synthesis and determination of the absolute configuration of (-)-idesolide

Hiroyuki Yamakoshi, Masatoshi Shibuya, Masaki Tomizawa, Yuji Osada, Naoki Kanoh, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

Abstract

(Chemical Equetion Presentation) The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)4-Bn-1-Bu-AZADO- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate. The absolute configuration of (-)-idesolide Is determined to be 2R,2' S, 3aS,7aR.

Original language	English
Pages (from-to)	980-983
Number of pages	4
Journal	Organic letters
Volume	12
Issue number	5
DOIs	https://doi.org/10.1021/ol9029676
Publication status	Published - 2010 Mar 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Total synthesis and determination of the absolute configuration of (-)-idesolide",

abstract = "(Chemical Equetion Presentation) The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)4-Bn-1-Bu-AZADO- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate. The absolute configuration of (-)-idesolide Is determined to be 2R,2' S, 3aS,7aR.",

author = "Hiroyuki Yamakoshi and Masatoshi Shibuya and Masaki Tomizawa and Yuji Osada and Naoki Kanoh and Yoshiharu Iwabuchi",

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T1 - Total synthesis and determination of the absolute configuration of (-)-idesolide

AU - Yamakoshi, Hiroyuki

AU - Shibuya, Masatoshi

AU - Tomizawa, Masaki

AU - Osada, Yuji

AU - Kanoh, Naoki

AU - Iwabuchi, Yoshiharu

PY - 2010/3/5

Y1 - 2010/3/5

N2 - (Chemical Equetion Presentation) The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)4-Bn-1-Bu-AZADO- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate. The absolute configuration of (-)-idesolide Is determined to be 2R,2' S, 3aS,7aR.

AB - (Chemical Equetion Presentation) The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)4-Bn-1-Bu-AZADO- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate. The absolute configuration of (-)-idesolide Is determined to be 2R,2' S, 3aS,7aR.

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