Huperzine alkaloids: forty years of total syntheses

Covering: up to 2023 Huperzine alkaloids are a group of natural products belonging to the Lycopodium alkaloids family. The representative member huperzine A has a unique structure and exhibits potent inhibitory activity against acetylcholine esterase (AChE). This subfamily of alkaloids provides a gr...

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Bibliographic Details
Published in:Natural product reports 2024-01, Vol.41 (1), p.59-84
Main Authors: Cheng, Bichu, Song, Lili, Chen, Fener
Format: Article
Language:English
Subjects:
Acetylcholinesterase
Alkaloids
Asymmetric synthesis
Biosynthesis
Chemistry
Huperzine A
Natural products
Organic chemistry
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Summary:Covering: up to 2023 Huperzine alkaloids are a group of natural products belonging to the Lycopodium alkaloids family. The representative member huperzine A has a unique structure and exhibits potent inhibitory activity against acetylcholine esterase (AChE). This subfamily of alkaloids provides a great opportunity for developing synthetic methodologies and asymmetric synthesis. The efforts towards the synthesis of huperzine A have cultivated dozens of total syntheses and a rich body of new chemistry. Impressive progress has also been made in the synthesis of other huperzine alkaloids. The total syntheses of huperzines B, U, O, Q and R, structure reassignment and total syntheses of huperzines K, M and N have been reported in the past decade. This review focuses on the synthetic organic chemistry and the biosynthesis and medicinal chemistry of huperzines are also covered briefly. This review discusses the synthetic chemistry of huperzine A, a potent inhibitor of acetylcholine esterase (AChE), followed by the advancements in other alkaloids of the family. The analogs and medicinal chemistry of huperzines are summarized.
ISSN:0265-0568
1460-4752
DOI:10.1039/d3np00029j