Transition-Metal-Mediated Chemo- and Stereoselective Total Synthesis of (-)-Galanthamine
Iain R Miller1, Neville J McLean1, Gamal A I Moustafa1
1School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K.
Abstract:
An asymmetric synthetic route to (-)-galanthamine (1), a pharmacologically active Amaryllidaceae alkaloid used for the symptomatic treatment of early onset Alzheimer's disease, was successfully established with very high levels of stereocontrol. The key to achieving high chemo- and stereo-selectivity in this approach was the use of transition-metal-mediated reactions, namely, enyne ring-closing metathesis, Heck coupling, and titanium-based asymmetric allylation.
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