Enantioselective total synthesis of the potent anti-inflammatory (+)-myrrhanol A

J Org Chem. 2009 Aug 21;74(16):6151-6. doi: 10.1021/jo901011m.

Abstract

The first total synthesis of potent anti-inflammatory polypodanes (+)-myrrhanol A (1), (+)-myrrhanone A (2), (+)-myrrhanone B (3), and (+)-myrrhanol B (4) has been achieved. Key steps in our convergent, highly stereocontrolled route are a Ti(III)-mediated radical cyclization of a chiral monoepoxide to furnish a bicyclic synthon that combines stereospecifically with an acyclic vinyl iodide via an intermolecular B-alkyl Suzuki-Miyaura cross-coupling.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / pharmacology
  • Cyclization
  • Stereoisomerism
  • Substrate Specificity
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Triterpenes
  • myrrhanol A