Asymmetric total synthesis of dendrobatid alkaloid 251F

J Am Chem Soc. 2002 Aug 28;124(34):9974-5. doi: 10.1021/ja027113y.

Abstract

The dendrobatid alkaloid (-)-251F was synthesized. The key steps of the synthesis were (1) an asymmetric Diels-Alder reaction to establish four of the necessary stereocenters in the target, (2) a ring-opening/ring-closing metathesis reaction to establish a key [3.3.0] bicyclic intermediate, and (3) an intramolecular Schmidt reaction.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Animals
  • Anura / metabolism

Substances

  • Alkaloids