Synthesis and structural reconfirmation of bacillamide B

Org Biomol Chem. 2015 Apr 14;13(14):4271-7. doi: 10.1039/c5ob00093a. Epub 2015 Mar 11.

Abstract

A concise total synthesis of the natural product bacillamide B was accomplished in 30% overall yield starting from L-cystine. The key step was a one-pot four-step process of thiazoline formation via a cascade disulfide cleavage/thiocarbonylation/Staudinger reduction/aza-Wittig reaction using β-azido disulfide and carboxylic acid as substrates. The absolute configuration of the natural bacillamide B was reconfirmed to be S and the specific optical rotation was revised to (-).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry*
  • Chemistry Techniques, Synthetic
  • Lactic Acid / chemistry
  • Stereoisomerism
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry*
  • Tryptamines / chemical synthesis*
  • Tryptamines / chemistry*

Substances

  • Biological Products
  • Thiazoles
  • Tryptamines
  • bacillamide B
  • Lactic Acid