title: Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids.
abstract: A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C(6) olefins, followed by N-O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids.
authors.affiliation: Departament de Química and Unitat de Cristallografia, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
authors.forename: Ramon
authors.initials: R
authors.lastname: Alibés
authors.forename: Pilar
authors.initials: P
authors.lastname: Blanco
authors.forename: Eva
authors.initials: E
authors.lastname: Casas
authors.forename: Montserrat
authors.initials: M
authors.lastname: Closa
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
authors.forename: Elena
authors.initials: E
authors.lastname: Sanfeliu
authors.forename: Angel
authors.initials: A
authors.lastname: Alvarez-Larena
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D041901:Stemonaceae / Q000737:chemistry*
chemical_list: D000470:Alkaloids