Please use this identifier to cite or link to this item:
http://hdl.handle.net/2445/128407
Title: | Synthesis of (±)-Serralongamine A and the Revised Structure of Huperzine N |
Author: | Saborit Villarroya, Gisela Bosch, Caroline Parella, Teodor Bradshaw, Ben Bonjoch i Sesé, Josep |
Keywords: | Alcaloides Catàlisi Síntesi orgànica Ciclització (Química) Productes naturals Metodologia Alkaloids Catalysis Organic synthesis Ring formation (Chemistry) Natural products Methodology |
Issue Date: | 1-Mar-2016 |
Publisher: | American Chemical Society |
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. |
Note: | Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.6b00025 |
It is part of: | Journal of Organic Chemistry, 2016, vol. 81, num. 6, p. 2629-2634 |
URI: | http://hdl.handle.net/2445/128407 |
Related resource: | https://doi.org/10.1021/acs.joc.6b00025 |
ISSN: | 0022-3263 |
Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) Articles publicats en revistes (Institut de Biomedicina (IBUB)) |
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