Concise enantioselective synthesis of ent-malbrancheamide B

J Am Chem Soc. 2009 Apr 1;131(12):4214-5. doi: 10.1021/ja900688y.

Abstract

A concise enantioselective synthesis of the fungal metabolite ent-malbrancheamide B was accomplished through the union of a C-prenylated proline derivative and a substituted indole pyruvic acid SEM enol ether, followed by a cationic double cyclization as the key step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Alkaloids / chemistry
  • Amides / chemistry
  • Biomimetic Materials / chemistry
  • Bridged Bicyclo Compounds / chemistry
  • Cations
  • Chemistry, Organic / methods*
  • Cyclization
  • Ethers / chemistry
  • Fungi / metabolism
  • Hydroxamic Acids / chemistry
  • Indole Alkaloids / chemical synthesis*
  • Models, Chemical
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aldehydes
  • Alkaloids
  • Amides
  • Bridged Bicyclo Compounds
  • Cations
  • Ethers
  • Hydroxamic Acids
  • Indole Alkaloids
  • malbrancheamide
  • malbrancheamide B