Angewandte Chemie. International edition in English 2012-12-07

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

Rodolphe Beaud, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent

Index: Angew. Chem. Int. Ed. Engl. 51(50) , 12546-50, (2012)

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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.Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.