Scalable Synthesis of a Key Intermediate for the Production of Pleuromutilin-Based Antibiotics

Org Lett. 2017 Sep 15;19(18):4980-4983. doi: 10.1021/acs.orglett.7b02476. Epub 2017 Aug 31.

Abstract

An improved synthesis of an eneimide, which is a useful precursor to pleuromutilin-based antibiotics, is reported. This synthesis proceeds in six steps and 17% overall yield (27% based on recovery of a key hydrindenone intermediate) and requires two fewer chromatography steps and five fewer days of reaction time than the previously reported route. The use of expensive, acutely toxic, and precious metal reagents or catalysts has been minimized.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Catalysis
  • Diterpenes
  • Molecular Structure
  • Pleuromutilins
  • Polycyclic Compounds

Substances

  • Anti-Bacterial Agents
  • Diterpenes
  • Polycyclic Compounds