Synthesis of (-)-epibatidine

Org Lett. 2001 Sep 20;3(19):3009-12. doi: 10.1021/ol016420q.

Abstract

The synthesis of (-)-epibatidine has been accomplished utilizing a highly exo-selective asymmetric hetero Diels-Alder reaction. The key steps employed to transform the resulting bicycle into the natural product include a fluoride-promoted fragmentation and a Hofmann rearrangement. Reaction: see text.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Analgesics, Non-Narcotic / chemical synthesis*
  • Analgesics, Non-Narcotic / chemistry
  • Animals
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Crystallography, X-Ray
  • Nicotinic Agonists / chemical synthesis
  • Nicotinic Agonists / chemistry
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Ranidae
  • Stereoisomerism

Substances

  • Alkaloids
  • Analgesics, Non-Narcotic
  • Bridged Bicyclo Compounds, Heterocyclic
  • Nicotinic Agonists
  • Pyridines
  • epibatidine