Tetrahedron

Enantioselective synthesis of dual 5-HT45-HT3 serotonergic azanoradamantane SC-52491

DP Becker, RK Husa, AE Moormann, CI Villamil…

Index: Becker, Daniel P.; Husa, Robert K.; Moormann, Alan E.; Villamil, Clara I.; Flynn, Daniel L. Tetrahedron, 1999 , vol. 55, # 40 p. 11787 - 11802

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Citation Number: 14

Abstract

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% ee