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

J Org Chem. 2022 Jan 21;87(2):1325-1334. doi: 10.1021/acs.joc.1c02638. Epub 2022 Jan 10.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids*
  • Alzheimer Disease*
  • Galantamine
  • Humans

Substances

  • Alkaloids
  • Galantamine