A short, efficient, and stereoselective total synthesis of a pyrrolidine alkaloid: (-)-codonopsinine

J Org Chem. 2007 Mar 16;72(6):2224-7. doi: 10.1021/jo061940q. Epub 2007 Feb 23.

Abstract

An efficient total synthesis of antibiotic (-)-codonopsinine 1 with an overall yield of 44% was achieved from d-alanine as a chiral template. The key steps in our strategy are modified Sharpless asymmetric dihydroxylation reaction and the highly stereoselective intramolecular acid-catalyzed amidocyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Pyrrolidines / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkaloids
  • Pyrrolidines
  • codonopsinine
  • pyrrolidine