Enantioselective synthesis of (-)-cis-clavicipitic acid

J Org Chem. 2007 Oct 12;72(21):8115-8. doi: 10.1021/jo071162h. Epub 2007 Sep 18.

Abstract

An enantioselective synthetic method for (-)-cis-clavicipitic acid (1) was reported. 1 was obtained in 10 steps (99% ee and 20% overall yield) from 1H-indole-3-carboxylic acid methyl ester (9) via asymmetric phase-transfer catalytic alkylation and diastereoselective Pd(II)-catalyzed intramolecular aminocyclization as key steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkylation
  • Azepines / chemical synthesis*
  • Azepines / chemistry
  • Azepines / isolation & purification
  • Catalysis
  • Claviceps / chemistry*
  • Ergot Alkaloids
  • Esters
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / isolation & purification
  • Molecular Structure
  • Palladium / chemistry
  • Phase Transition
  • Stereoisomerism

Substances

  • Alkaloids
  • Azepines
  • Ergot Alkaloids
  • Esters
  • Indoles
  • clavicipitic acid
  • indole-3-carboxylic acid
  • Palladium