Stereocontrolled total synthesis of (-)-kainic acid. Regio- and stereoselective lithiation of pyrrolidine ring with the (+)-sparteine surrogate

Yasuhiro Morita, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

53 Citations (Scopus)

Abstract

(Chemical Equation Presented) A stereocontrolled total synthesis of (-)-kainic acid is described. cis-3,4-Disubstituted pyrrolidine ring was constructed by [3 + 2] cycloaddition of azomethine ylide with chiral butenolide. The crucial introduction of carboxyl group at the C-2 position was executed by regio- and stereoselective lithiation of the pyrrolidine ring in the presence of a (+)-sparteine surrogate followed by trapping with carbon dioxide.

Original languageEnglish
Pages (from-to)4337-4340
Number of pages4
JournalOrganic letters
Volume7
Issue number20
DOIs
Publication statusPublished - 2005 Sep 29
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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