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Enantioselective Synthesis Of Dual Serotonergic Azanoradamantane Sc-52491, Daniel Becker, Robert K. Husa, Alan E. Moormann, Clara I. Villamil

Chemistry: Faculty Publications and Other Works

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.