An efficient, three-component, microwave-mediated cyclization to prepare the 3,5-disubstituted 2H-pyrrol-2-one core of the bisindole alkaloid, violacein (1  ), is described. Results indicate an iterative, thermally driven, condensation of a gamma-ketoester (2  ), ammonium acetate and isatin (3  ) in polyethylene glycol. This methodology is an effective and environmentally benign route to prepare violacein and a series of related analogs in 2-4 synthetic steps. Preliminary biological data for the small library of analogs is also reported.

Microwave mediated, three-component synthesis of disubstituted 2H-pyrrol-2-ones: Preparation of violacein and related analogs

248th National Meeting (2014)

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