title: Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide.
abstract: A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide.
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
authors.forename: Gisela G
authors.initials: GG
authors.lastname: Bardají
authors.forename: Mariona
authors.initials: M
authors.lastname: Cantó
authors.forename: Ramón
authors.initials: R
authors.lastname: Alibés
authors.forename: Pau
authors.initials: P
authors.lastname: Bayón
authors.forename: Félix
authors.initials: F
authors.lastname: Busqué
authors.forename: Pedro
authors.initials: P
authors.lastname: de March
authors.forename: Marta
authors.initials: M
authors.lastname: Figueredo
authors.forename: Josep
authors.initials: J
authors.lastname: Font
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D001381:Azepines / Q000138:chemical synthesis*; D001572:Benzofurans / Q000737:chemistry*; D019665:Euphorbiaceae; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D001572:Benzofurans; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D010880:Piperidines; C438745:menisdaurilide; C012607:virosecurinine; C000785:securinine