A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamo
to's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetri
c synthesis of azanoradamantane benzamide SC-52491 was carried out employin
g Helmchen's asymmetric Diels-Alder methodology to construct all four conti
guous asymmetric centers with the correct relative stereochemistry and in 9
9.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.