Total synthesis of (-)-kainic acid via intramolecular michael addition: A second-generation route

Hiroshi Sakaguchi, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

A total synthesis of (-)-kainic acid starting from the commercially available 2-azetidinone is described. The key δ-lactone intermediate was concisely prepared from the commercially available azetidinone through the Reformatsky-type reaction and an introduction of a glycine moiety. The construction of the functionalized pyrrolidine ring was executed by a one-pot sequential elimination-Michael addition protocol of a β-amino-δ- lactone intermediate with high diastereoselectivity.

Original languageEnglish
Pages (from-to)1711-1714
Number of pages4
JournalOrganic letters
Volume10
Issue number9
DOIs
Publication statusPublished - 2008 May 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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