Total synthesis of (-)-stemonine

Org Lett. 2003 Sep 4;5(18):3361-4. doi: 10.1021/ol035368q.

Abstract

[reaction: see text] An enantioselective total synthesis of (-)-stemonine (1) is reported via a convergent assembly of the acyclic precursor 2. Key transformations include a Staudinger-aza-Wittig reaction to form the central perhydroazepine ring system and an iodine-induced tandem cyclization to construct the pyrrolidino-butyrolactone framework.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Azepines / chemistry
  • Cyclization
  • Iodine / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Stemonaceae / chemistry*
  • Stereoisomerism

Substances

  • Alkaloids
  • Azepines
  • Lactones
  • Pyrrolidines
  • stemonine
  • Iodine
  • hexahydroazepine