Transition-Metal-Mediated Chemo- and Stereoselective Total Synthesis of (−)-Galanthamine

Autor: Miller, Iain R., McLean, Neville J., Moustafa, Gamal A. I., Ajavakom, Vachiraporn, Kemp, Stephen C., Bellingham, Richard K., Camp, Nicholas P., Brown, Richard C. D.
Zdroj: The Journal of Organic Chemistry; January 2022, Vol. 87 Issue: 2 p1325-1334, 10p
Abstrakt: An asymmetric synthetic route to (−)-galanthamine (1), a pharmacologically active Amaryllidaceaealkaloid 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.
Databáze: Supplemental Index