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 journalArticle

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 languageEnglish
Pages (from-to)8609-8615
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number43
DOIs
Publication statusPublished - Nov 21 2012
Externally publishedYes

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Stereoisomerism
activity (biology)
routes
synthesis
dysidiolide

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Stereoconvergent route to chiral cyclohexenone building blocks : Formal synthesis of (-)-dysidiolide. / Moustafa, Gamal A I; Kamada, Yasumasa; Tanaka, Tetsuaki; Yoshimitsu, Takehiko.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 43, 21.11.2012, p. 8609-8615.

Research output: Contribution to journalArticle

Moustafa, Gamal A I ; Kamada, Yasumasa ; Tanaka, Tetsuaki ; Yoshimitsu, Takehiko. / Stereoconvergent route to chiral cyclohexenone building blocks : Formal synthesis of (-)-dysidiolide. In: Organic and Biomolecular Chemistry. 2012 ; Vol. 10, No. 43. pp. 8609-8615.
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