Tandem gold-catalyzed dehydrative cyclization/diels-alder reactions: facile access to indolocarbazole alkaloids

Organic Letters
Nicholas V BorreroAaron Aponick

Abstract

A gold-catalyzed synthesis of cyclic 2-oxodienes from readily prepared propargyl alcohols and the subsequent Diels-Alder reaction are reported. The dehydrative cyclization reactions proceeded smoothly, and the dienes formed in situ were demonstrated to undergo cycloaddition with a variety of dienophiles. This method offers a new strategy for the synthesis of indolocarbazole alkaloids, whereby the convergent synthetic design allows for differentiation between the indole nitrogens.

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