An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B

J Am Chem Soc. 2013 Jul 31;135(30):10890-3. doi: 10.1021/ja405548b. Epub 2013 Jul 18.

Abstract

This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.

Publication types

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

MeSH terms

  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry*
  • Organic Chemicals
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Indole Alkaloids
  • Organic Chemicals
  • citrinadin A