title: Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (-)-Huperzine N.
abstract: A unified strategy for the synthesis of the cis-phlegmarine group of alkaloids is presented, leading to the first synthesis of serratezomine E (1) as well as the putative structure of huperzine N (2). A contrasteric hydrogenation method was developed based on the use of Wilkinson's catalyst, which allowed the facial selectivity of standard hydrogenation to be completely overturned. Calculations were performed to determine the mechanism, and structures for huperzines M and N are reassigned.
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: Departamento de Química Orgánica I, Universidad del País Vasco , Manuel Lardizábal 3, 20018 San Sebastián, Spain.
authors.forename: Béla
authors.initials: B
authors.lastname: Fiser
authors.affiliation: Departamento de Química Orgánica I, Universidad del País Vasco , Manuel Lardizábal 3, 20018 San Sebastián, Spain.
authors.forename: Enrique
authors.initials: E
authors.lastname: Gómez-Bengoa
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: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006865:Hydrogenation; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011804:Quinolines; D012717:Sesquiterpenes; C542896:serratezomine E; C050426:huperzine A