A general efficient strategy for cis-3a-aryloctahydroindole alkaloids via stereocontrolled ZnBr(2)-catalyzed rearrangement of 2,3-aziridino alcohols

Org Lett. 2003 Jun 26;5(13):2319-21. doi: 10.1021/ol0346685.

Abstract

A short and general approach to the cis-3a-aryloctahydroindole alkaloids has been developed on the basis of a key stereocontrolled ZnBr(2)-catalyzed rearrangement of 2,3-aziridino alcohols. Two representative members, (+/-)-crinane and (+/-)-mesembrine, have been synthesized in 15% and 11% overall yields, respectively. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Aziridines / chemistry*
  • Catalysis
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Stereoisomerism
  • Zinc Compounds / chemistry*

Substances

  • Alcohols
  • Aziridines
  • Indole Alkaloids
  • Zinc Compounds