Short total synthesis of (-)-kainic acid

Org Lett. 2014 May 2;16(9):2550-3. doi: 10.1021/ol5009526. Epub 2014 Apr 17.

Abstract

A short total synthesis of (-)-kainic acid has been developed involving a novel diastereofacial differentiating Cu-catalyzed Michael addition-cyclization reaction, which provided access to a chiral pyrroline in a highly stereoselective manner. The chiral pyrroline was converted to (-)-kainic acid via the stereoselective 1,4-reduction of the pyrroline double bond in three steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry
  • Kainic Acid / chemical synthesis*
  • Kainic Acid / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Pyrroles / chemistry
  • Stereoisomerism

Substances

  • Pyrroles
  • pyrroline
  • Copper
  • Kainic Acid