title: Synthesis of the putative structure of 15-oxopuupehenoic acid.
abstract: Synthesis of the putative structure of the marine natural 15-oxopuupehenoic acid has been achieved starting from commercial (-)-sclareol. Key steps of the synthetic sequence are the Robinson annulation of a β-ketoester and methyl vinyl ketone and an unprecedented cyclization of the resulting α,β-enone, which is mediated by tin(IV) chloride in the presence of N-phenylselenophthalimide. The physical properties of the synthetic compound are somewhat different from those reported for the natural product.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada , 18071 Granada, Spain.
authors.forename: Ettahir
authors.initials: E
authors.lastname: Boulifa
authors.forename: Antonio
authors.initials: A
authors.lastname: Fernández
authors.forename: Esteban
authors.initials: E
authors.lastname: Alvarez
authors.forename: Ramón
authors.initials: R
authors.lastname: Alvarez-Manzaneda
authors.forename: Ahmed I
authors.initials: AI
authors.lastname: Mansour
authors.forename: Rachid
authors.initials: R
authors.lastname: Chahboun
authors.forename: Enrique
authors.initials: E
authors.lastname: Alvarez-Manzaneda
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D003500:Cyclization; D004224:Diterpenes / Q000737:chemistry*; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D017971:Tin Compounds / Q000737:chemistry
chemical_list: C000596134:15-oxopuupehenoic acid; D001688:Biological Products; D004224:Diterpenes; C000596135:N-phenylselenophthalimide; D010797:Phthalimides; D012717:Sesquiterpenes; D017971:Tin Compounds; C023599:stannous chloride; C070760:sclareol