Synthetic strategies for the construction of enantiomeric azanoradamantanes

The amino azanoradamantane hexahydro-2,5b-methano-1H-3aS, 3aa,6aa-cyclopenta-[c]pyrrole-4a-amine 1 and the corresponding enantiomer ent-1 have been prepared along with benzamide derivatives SC-52491 and SC-52490, respectively, which are of pharmaceutical interest. The key meso-azabicyclo[3.3.0] intermediate 3 was prepared via three separate routes: a [3+2] cycloaddition route, a radical cyclization/ionic cyclization route, and a reductive Pauson-Khand route. Copyright (C) 1996 Elsevier Science Ltd