Formal [1 + 2 + 3] Annulation: Domino Access to Carbazoles and Indolocarbazole Alkaloids

Abstract

A new formal [1 + 2 + 3] annulation of o-alkenyl arylisocyanides with α, β-unsaturated ketones under metal-, base-, and acid-free conditions is disclosed. This domino reaction provides a general protocol for the efficient and practical synthesis of a wide range of carbazole derivatives from readily available starting materials in a single operation. Furthermore, this methodology was used as the key step in a protecting-group-free synthesis of indolocarbazole alkaloids arcyriaflavin A and racemosin B.