title: Flexible approach to stemona alkaloids: total syntheses of (-)-stemospironine and three new diastereoisomeric analogs.
abstract: Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs have been completed through a flexible strategy devised for Stemona alkaloids. The azabicycle 7 is the pivotal intermediate, from which the sequence splits according to each particular target. The most remarkable differential feature for stemospironine is the installation of the spiranic γ-lactone through an intramolecular Horner-Wadsworth-Emmons olefination. The configuration of the stereogenic center at C-11 was controlled by fine-tuning of the synthetic sequence.
authors.affiliation: Universitat Autònoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain.
authors.forename: Nuria
authors.initials: N
authors.lastname: Bardají
authors.forename: Francisco
authors.initials: F
authors.lastname: Sánchez-Izquierdo
authors.forename: Ramón
authors.initials: R
authors.lastname: Alibés
authors.forename: Josep
authors.initials: J
authors.lastname: Font
authors.forename: Félix
authors.initials: F
authors.lastname: Busqué
authors.forename: Marta
authors.initials: M
authors.lastname: Figueredo
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D041901:Stemonaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C437124:stemospironine