Enantioselective Synthesis of Dual Serotonergic Azanoradamantane SC-52491

A racemic synthesis of azanoradamantane (±)-3 was accomplished via Yamamoto\u27s MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen\u27s asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e