Total synthesis of (+)-epiquinamide

Org Lett. 2005 Sep 1;7(18):4005-7. doi: 10.1021/ol0515715.

Abstract

The stereoselective total synthesis of the novel quinolizidine alkaloid (+)-epiquinamide is presented, starting from the amino acid l-allysine ethylene acetal. Key steps in the synthesis involved a highly diastereoselective N-acyliminium ion allylation and a ring-closing metathesis reaction to provide the bicyclic skeleton. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Cyclization
  • Molecular Conformation
  • Molecular Structure
  • Quinolizines / chemical synthesis*
  • Quinolizines / chemistry
  • Stereoisomerism

Substances

  • Alkaloids
  • Quinolizines
  • epiquinamide