Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring

J Org Chem. 2002 Oct 18;67(21):7255-60. doi: 10.1021/jo020386r.

Abstract

The first syntheses of the alkaloids (-)-mehranine (3), (+)-voaphylline/conoflorine (4), (+)-N(a)-methylvoaphylline/hecubine (5), and (-)-lochnericine (2) were achieved by stereoselective epoxidation starting from (-)-tabersonine (1), through intermediates with the aspidospermane and quebrachamine skeleton.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry*
  • Epoxy Compounds / chemistry*
  • Indicators and Reagents
  • Indole Alkaloids*
  • Indoles / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Oxidation-Reduction
  • Quinolines*
  • Stereoisomerism
  • Vinca Alkaloids / chemical synthesis*
  • Vinca Alkaloids / chemistry

Substances

  • Alkaloids
  • Epoxy Compounds
  • Indicators and Reagents
  • Indole Alkaloids
  • Indoles
  • Quinolines
  • Vinca Alkaloids
  • quebrachamine
  • aspidospermine