A General Efficient Strategy for <i>cis</i>-3a-Aryloctahydroindole Alkaloids via Stereocontrolled ZnBr₂-Catalyzed Rearrangement of 2,3-Aziridino Alcohols

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]