Enantiospecific total synthesis of (-)-bengamide E

Chem Asian J. 2013 Feb;8(2):488-93. doi: 10.1002/asia.201200999. Epub 2012 Dec 3.

Abstract

Total synthesis of the polyhydroxy caprolactam amide natural product, bengamide E, is accomplished starting from tartaric acid. Key reactions in the synthesis include desymmetrization of the bis(dimethylamide) unit of tartaric acid, Zn(BH(4))(2)-mediated anti-selective reduction, and a Horner-Wadsworth-Emmons olefination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Amides / chemistry
  • Azepines / chemical synthesis*
  • Azepines / chemistry
  • Caprolactam / chemistry
  • Stereoisomerism
  • Tartrates / chemistry

Substances

  • Alkenes
  • Amides
  • Azepines
  • Tartrates
  • bengamide E
  • Caprolactam
  • tartaric acid