An expeditious total synthesis of (+/-)-stenine

J Am Chem Soc. 2005 Nov 16;127(45):15712-3. doi: 10.1021/ja055629m.

Abstract

(+/-)-Stenine was synthesized in eight steps from a known ketophosphonate reagent. The key step was an exo-selective Diels-Alder/intramolecular Schmidt domino reaction that afforded three of the four rings and four stereocenters in a single reaction.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Molecular Structure

Substances

  • Alkaloids
  • stenine