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

Saborit Villarroya, GiselaBosch, CarolineParella, TeodorBradshaw, BenBonjoch i Sesé, Josep2019-02-192019-02-192016-03-010022-3263https://hdl.handle.net/2445/128407A 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.6 p.application/pdfeng(c) American Chemical Society , 2016AlcaloidesCatàlisiSíntesi orgànicaCiclització (Química)Productes naturalsMetodologiaAlkaloidsCatalysisOrganic synthesisRing formation (Chemistry)Natural productsMethodologySynthesis of (±)-Serralongamine A and the Revised Structure of Huperzine Ninfo:eu-repo/semantics/article6607142019-02-19info:eu-repo/semantics/openAccess26927208