Stereocontrolled total synthesis of (-)-kainic acid

Hiroshi Sakaguchi, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

62 Citations (Scopus)

Abstract

A stereocontrolled total synthesis of (-)-kainic acid is described. A fully functionalized trisubstituted pyrrolidine ring was constructed by ring-closing metathesis of an acrylate derivative followed by an intramolecular Michael addition of the resultant α,β-unsaturated lactone with high diastereoselectivity. Two alternative protocols for the construction of the α,β-unsaturated lactone were also developed.

Original languageEnglish
Pages (from-to)1635-1638
Number of pages4
JournalOrganic letters
Volume9
Issue number9
DOIs
Publication statusPublished - 2007 Apr 26

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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