Total synthesis of the antibiotic elansolid B1

Org Lett. 2014 Jan 17;16(2):568-71. doi: 10.1021/ol403441c. Epub 2014 Jan 7.

Abstract

The antibiotic elansolid B1 was prepared by a convergent strategy that relied on a highly diastereoselective, biomimetic intramolecular Diels-Alder cycloaddition (IMDA) that furnished the tetrahydroindane unit. Other key features are a double Sonogashira cross-coupling and a substrate-controlled Yamamoto aldol reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Biomimetics
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • Macrolides
  • elansolid B1