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Synfacts 2007(9): 0905-0905  
DOI: 10.1055/s-2007-968837
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Galanthamine

Contributor(s): Philip Kocienski
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
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Publication History

Publication Date:
23 August 2007 (online)

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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).