Expedient total synthesis of pyrrothine natural products and analogs

Org Biomol Chem. 2007 Jan 21;5(2):344-8. doi: 10.1039/b616411k. Epub 2006 Nov 27.

Abstract

This paper describes an expedient and straightforward total synthesis of the two pyrrothine natural products holomycin (7 steps, 11% overall) and xenorhabdin I (7 steps, 11% overall) and analogs thereof via a common late-stage intermediate. The pathway proceeds via the pyrrothine hydrochloride intermediate (6 steps, 17% overall) which also gave access to very fast synthesis of analogs as demonstrated by the synthesis of , and (7 steps, 11-12% overall).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / pharmacology*
  • Chemistry, Organic / methods
  • Chromatography, Thin Layer
  • DNA-Directed RNA Polymerases / metabolism
  • Lactams / chemistry*
  • Models, Chemical
  • Pseudomonas / metabolism
  • RNA, Bacterial / biosynthesis
  • Streptomyces / metabolism
  • Xenorhabdus / metabolism*

Substances

  • Anti-Bacterial Agents
  • Lactams
  • RNA, Bacterial
  • holomycin
  • DNA-Directed RNA Polymerases