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

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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