Synthesis of the bicyclic welwitindolinone core via an alkylation/cyclization cascade reaction

Org Lett. 2009 Nov 19;11(22):5330-3. doi: 10.1021/ol902173g.

Abstract

Synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization reaction is reported. The key step involves a one pot Lewis acid-mediated alkylation of a silylketene aminal with a furan alcohol followed by an intramolecular cyclization. The reaction is stereoselective and takes place at low temperature. The cycloadduct was highly functionalized and contains the welwitindolinone core structure.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Alkylation
  • Crystallography, X-Ray
  • Cyclization
  • Indole Alkaloids
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Models, Molecular
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Stereoisomerism

Substances

  • Alkaloids
  • Indole Alkaloids
  • Indoles
  • Nitriles
  • welwitindolinone A
  • welwitindolinone B
  • welwitindolinone C isothiocyanate