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.
Becker, Daniel; Husa, Robert K.; Moormann, Alan E.; and Villamil, Clara I.. Enantioselective Synthesis of Dual Serotonergic Azanoradamantane SC-52491. Tetrahedron Letters, 55, 40: , 1999. Retrieved from Loyola eCommons, Chemistry: Faculty Publications and Other Works, http://dx.doi.org/10.1016/S0040-4020(99)00680-8
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