FeCl3-mediated Friedel-Crafts hydroarylation with electrophilic N-acetyl indoles for the synthesis of benzofuroindolines

Angew Chem Int Ed Engl. 2012 Dec 7;51(50):12546-50. doi: 10.1002/anie.201206611. Epub 2012 Nov 4.

Abstract

IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl(3) features a rare example of the electrophilic reactivity of the indole core in a Friedel-Crafts reaction. This indole umpolung allows us straightforward access to the tetracyclic benzofuroindoline motif found in the natural product diazonamide A, which is a potent antitumor agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Catalysis
  • Chlorides / chemistry*
  • Ferric Compounds / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Oxazoles / chemical synthesis
  • Oxazoles / chemistry
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Chlorides
  • Ferric Compounds
  • Heterocyclic Compounds, 4 or More Rings
  • Indoles
  • Oxazoles
  • diazonamide A
  • indoline
  • indole
  • ferric chloride