Synthesis of indole alkaloid analogues: novel domino stereoselective electrophile addition--cyclizations of tryptophan-derived alpha-amino nitriles

J Org Chem. 2007 Jul 6;72(14):5395-8. doi: 10.1021/jo070684u. Epub 2007 Jun 19.

Abstract

The synthesis of new indole alkaloid analogues, containing a 1,2,4,5,10b,10c-hexahydropyrrolo[1',2',3':1,9a,9]imidazo[1,2-a]indole skeleton, via highly stereoselective novel domino cyclative halogenation or prenylation reactions of tryptophan-derived alpha-amino nitriles, is described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Bromine / chemistry
  • Chlorine / chemistry
  • Cyclization
  • Electrons
  • Imidazoles / chemistry
  • Indole Alkaloids / chemical synthesis
  • Indole Alkaloids / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitriles / chemistry*
  • Stereoisomerism
  • Tryptophan / chemistry*

Substances

  • Imidazoles
  • Indole Alkaloids
  • Nitriles
  • Chlorine
  • Tryptophan
  • Bromine