Synthesis of (-)-9,10-epi-stemoamide

J Org Chem. 2004 Oct 29;69(22):7734-6. doi: 10.1021/jo049083i.

Abstract

An efficient synthesis of (-)-9,10-epi-stemoamide has been accomplished in nine steps and 13% overall yield. The synthesis features a lithium hydroxide-promoted fragmentation and an intramolecular 7-exo-trig radical cyclization.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Catalysis
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry
  • Stemonaceae / chemistry
  • Stereoisomerism

Substances

  • 9,10-epi-stemoamide
  • Alkaloids
  • Heterocyclic Compounds, 3-Ring