Preparation and synthetic applications of 2-halotryptamines: Synthesis of elacomine and isoelacomine

The preparation of 2-halotryptamines from tryptamine is described. New stereoselective intramolecular iminium ion spirocyclization methodology for the construction of spiro[pyrrolidine-3,3'-oxindoles] is outlined in synthetic studies of elacomine (1) and isoelacomine (2).