Total syntheses of the resorcylic acid lactone neocosmosin A and its enantiomer

J Org Chem. 2015 May 1;80(9):4828-33. doi: 10.1021/acs.joc.5b00590. Epub 2015 Apr 13.

Abstract

A total synthesis of the structure, 1, assigned to the recently reported resorcylic acid lactone (RAL) neocosmosin A has been established. Olefin-cross metathesis, ring-closing metathesis, palladium-catalyzed Meinwald rearrangement, and Mitsunobu esterification reactions were used as key steps. A late-stage and simple modification to the reaction sequence also provided compound ent-1 that, in fact, represents the true structure of the natural product.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Conformation
  • Resorcinols / chemical synthesis*
  • Resorcinols / chemistry
  • Stereoisomerism

Substances

  • Lactones
  • Resorcinols
  • neocosmosin A