title: Synthesis of (±)-Serralongamine A and the Revised Structure of Huperzine N.
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.
authors.affiliation: Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona , Av. Joan XXIII s/n, 08028-Barcelona, Spain.
authors.forename: Gisela V
authors.initials: GV
authors.lastname: Saborit
authors.affiliation: Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona , Av. Joan XXIII s/n, 08028-Barcelona, Spain.
authors.forename: Caroline
authors.initials: C
authors.lastname: Bosch
authors.affiliation: Servei de Ressonància Magnètica Nuclear, Universitat Autònoma de Barcelona , 08193-Bellatera, Barcelona, Spain.
authors.forename: Teodor
authors.initials: T
authors.lastname: Parella
authors.affiliation: Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona , Av. Joan XXIII s/n, 08028-Barcelona, Spain.
authors.forename: Ben
authors.initials: B
authors.lastname: Bradshaw
authors.affiliation: Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona , Av. Joan XXIII s/n, 08028-Barcelona, Spain.
authors.forename: Josep
authors.initials: J
authors.lastname: Bonjoch
mesh_terms: D002384:Catalysis; D006865:Hydrogenation; D032502:Lycopodium / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D011804:Quinolines; D012717:Sesquiterpenes; C000611155:cis-5-oxodecahydroquinoline; C000611154:huperzine N; C000611153:serralongamine A