Flow Conditions‐Controlled Divergent Oxidative Cyclization of Reticuline‐Type Alkaloids to Aporphine and Morphinandienone Natural Products

Described herein is a divergent continuous-flow approach for the biomimetic oxidative cyclization of reticuline-type alkaloids to aporphine and morphinandienone natural products using hypervalent iodine(III) reagents. The method was based on detailed knowledge reaction mechanisms in order develop robust conditions toward selective synthesis either or products. In this frame, we exploited ability HFIP stabilize radical cation intermediates activate oxidants flow such as glaucine, rogersine nantenine. On other hand, established that PhI(OAc)(OTf), prepared by action TMSOTf PhI(OAc)2, powerful oxidant sebiferine amurine.