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Synfacts 2007(9): 0905-0905
DOI: 10.1055/s-2007-968837
DOI: 10.1055/s-2007-968837
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (-)-Galanthamine
V. Satcharoen, N. J. McLean, S. C. Kemp, N. P. Camp, R. C. D. Brown*
University of Southampton and eli Lilly Research Centre, Surrey, UK
Further Information
Publication History
Publication Date:
23 August 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200709/lookinside/thumbnails/10.1055-s-2007-968837-1.jpg)
Significance
(-)-Galanthamine is an Amaryllidaceae alkaloid that displays competitive reversible inhibition of acetylcholine esterase and allosteric potentiation of nicotinic acetylcholine receptors. It is in clinical use for the treatment of Alzheimer’s diasease. The Brown synthesis is based on two key steps: an enyne ring-closing metathesis (A to B) and a Heck reaction to construct the five-membered oxacycle (C to D).