Total synthesis of (-)-nakadomarin A

Chem Commun (Camb). 2011 Sep 28;47(36):10037-9. doi: 10.1039/c1cc13665h. Epub 2011 Aug 8.

Abstract

A highly diastereoselective bifunctional organocatalyst controlled Michael addition, a nitro-Mannich/lactamization cascade, a furan N-acyliminium cyclisation, a sequential alkyne RCM/syn-reduction and an alkene RCM has allowed a 19 step, highly stereoselective synthesis of (-)-nakadomarin A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Alkynes / chemistry
  • Carbolines / chemical synthesis*
  • Carbolines / chemistry
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Alkenes
  • Alkynes
  • Carbolines
  • nakadomarin A