Tandem Wittig-ene reaction approach to kainic acid

J Org Chem. 2009 May 1;74(9):3591-4. doi: 10.1021/jo900196t.

Abstract

The first example of a tandem Wittig-intramolecular ene reaction approach and its application toward the synthesis of kainic acid is reported. The synthetic pathway involves conversion of prenyl bromide into phosphorane 3, followed by one-pot Wittig olefination and an ene reaction with glyoxalic acid to give the cis fused pyrrolidine skeleton of kainic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Kainic Acid / chemical synthesis*
  • Pyrrolidinones / chemical synthesis
  • Pyrrolidinones / chemistry
  • Stereoisomerism

Substances

  • Pyrrolidinones
  • Kainic Acid