One-step assembly of alkoxypyrroloindolines via iodine-catalyzed alkoxycyclization of indole derivatives

Abstract

Herein we report an iodine-catalyzed alkoxycyclization of tryptamine derivatives under mild reaction conditions. This method distinguished itself by providing a catalytic, one-step assembly of diversely functionalized C3a-alkoxypyrroloindolines as well as dihydrofuran and lactone fused indolines. Mechanistic studies suggest that an ionic pathway is operative and this probably accounts for the diastereospecificity of all isolated cycloadducts.