Enantioselective synthesis of dual 5-HT4/5-HT3 serotonergic azanoradamantane SC-52491

Article abstract of DOI:10.1016/S0040-4020(99)00680-8

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