Synthesis of Tetrahydropyrroloiminoquinone Alkaloids Based on Electrochemically Generated Hypervalent Iodine Oxidative Cyclization

An approach to the synthesis of the tetrahydropyrrololminoquinone alkaloids has been developed and applied to the preparation of N-1-beta-D-ribofuranosyltetrahydropyrroloiminoquinones. The strategy utilizes oxidative cyclization of aryl-methoxyamides by hypervalent iodine to construct the quinoline framework shared by members of this alkaloid family. The hypervalent iodine oxidant is generated in situ by anodic oxidation of iodobenzene.