Application of furyl-stabilized sulfur ylides to a concise synthesis of 8a-epi-swainsonine

Chem Commun (Camb). 2008 Jan 7:(1):120-2. doi: 10.1039/b713447a.

Abstract

The total synthesis of 8a-epi-swainsonine has been achieved in 20% overall yield from R-glyceraldehyde dimethylacetonide 3 through epoxidation with the achiral furyl-substituted sulfonium ylide 2d as one of the key steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Catalysis
  • Molecular Structure
  • Stereoisomerism
  • Sulfur Compounds / chemistry*
  • Swainsonine / chemical synthesis*
  • Swainsonine / chemistry
  • Thiophenes / chemistry

Substances

  • Aldehydes
  • Sulfur Compounds
  • Thiophenes
  • tetrahydrothiophene
  • Swainsonine