Concise formal synthesis of (-)-peduncularine via ring-closing metathesis

Org Lett. 2003 Sep 18;5(19):3523-5. doi: 10.1021/ol0354066.

Abstract

[reaction: see text] A synthesis of the 6-aza[3.2.1]bicyclooctene (-)-2 has been completed by a short sequence of reactions that required only six operations from (S)-malic acid and featured a novel ring-closing metathesis to form the bridged bicyclic ring. Because 2 was previously converted into (-)-peduncularine (1), its preparation constitutes a formal enantioselective synthesis of 1.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Aza Compounds / chemical synthesis
  • Bridged Bicyclo Compounds / chemical synthesis
  • Indole Alkaloids
  • Indoles / chemical synthesis*
  • Malates / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkaloids
  • Aza Compounds
  • Bridged Bicyclo Compounds
  • Indole Alkaloids
  • Indoles
  • Malates
  • peduncularine
  • malic acid