Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: application to the synthesis of (-)-sedamine

J Org Chem. 2004 Nov 26;69(24):8514-7. doi: 10.1021/jo048848j.

Abstract

Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (-)-lobeline to (-)-sedamine in high overall yield.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Lobeline / chemical synthesis
  • Lobeline / chemistry*
  • Molecular Structure
  • Piperidines / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkaloids
  • Piperidines
  • sedamine
  • Lobeline