Stereoconvergent route to chiral cyclohexenone building blocks: Formal synthesis of (-)-dysidiolide

Gamal A.I. Moustafa; Yasumasa Kamada; Tetsuaki Tanaka; Takehiko Yoshimitsu

doi:10.1039/c2ob26532j

Stereoconvergent route to chiral cyclohexenone building blocks: Formal synthesis of (-)-dysidiolide

Gamal A.I. Moustafa, Yasumasa Kamada, Tetsuaki Tanaka, Takehiko Yoshimitsu

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

2 Citations (Scopus)

Abstract

A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.

Original language	English
Pages (from-to)	8609-8615
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	43
DOIs	https://doi.org/10.1039/c2ob26532j
Publication status	Published - Nov 21 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c2ob26532j

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abstract = "A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.",

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AU - Moustafa, Gamal A.I.

AU - Kamada, Yasumasa

AU - Tanaka, Tetsuaki

AU - Yoshimitsu, Takehiko

PY - 2012/11/21

Y1 - 2012/11/21

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