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2016-03-01

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/128407

Synthesis of (±)-Serralongamine A and the Revised Structure of Huperzine N

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Abstract

A revised structure for the Lycopodium alkaloid huperzine N is proposed and confirmed by synthesis. The key synthetic steps involve an epimerization of a cis-5-oxodecahydroquinoline to the corresponding trans isomer and a coupling, followed by a diastereoselective hydrogenation using Wilkinson's catalyst to incorporate the pyridylmethyl moiety. This route allowed the alkaloid serralongamine A to be synthesized for the first time, and two additional steps led to the revised structure of huperzine N, both products bearing an unusual decahydroquinoline stereostructure.

Related resource

https://doi.org/10.1021/acs.joc.6b00025

Subject

Alcaloides, Catàlisi, Síntesi orgànica, Ciclització (Química), Productes naturals, Metodologia

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Alkaloids, Catalysis, Organic synthesis, Ring formation (Chemistry), Natural products, Methodology

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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SABORIT VILLARROYA, Gisela, et al. Synthesis of (±)-Serralongamine A and the Revised Structure of Huperzine N. Journal of Organic Chemistry. 2016. Vol. 81, num. 6, pags. 2629-2634. ISSN 0022-3263. [consulted: 7 of October of 2026]. Available at: https://hdl.handle.net/2445/128407

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