Physical Sciences and Mathematics Commons^™

Synthetic Strategies For The Construction Of Enantiomeric Azanoradamantanes, Daniel Becker, Roger Nosal, Daniel L. Zabrowski, Daniel Flynn

Chemistry: Faculty Publications and Other Works

The amino azanoradamantane hexahydro-2,5b-methano-IH-3aS,3aa,6aa-cyclopenta-[clpyrrole-4a-amine 1and the corresponding enantiomer ent-1 have been prepared along with benzamide derivatives SC-52491and 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.