title: Sequential nucleophilic addition/intramolecular cycloaddition to chiral nonracemic cyclic nitrones: a highly stereoselective approach to polyhydroxynortropane alkaloids.
abstract: Two new polyhydroxylated nortropane analogues closely related with Calystegines have been prepared in excellent chemical yields and complete selectivity. A synthetic strategy based on consecutive nucleophilic allylation, oxidation, and intramolecular dipolar cycloaddition was developed. The formation of key intermediate cycloadducts were observed to take place through the recently confirmed thermally induced 2-aza-Cope rearrangement of nitrones.
authors.affiliation: Servicio de Resonancia Magnetica Nuclear, CEQMA, Instituto de Sintesis Quimica y Catalisis Homogenea, Universidad de Zaragoza, CSIC, 50009 Zaragoza, Aragón, Spain.
authors.forename: Ignacio
authors.initials: I
authors.lastname: Delso
authors.forename: Tomás
authors.initials: T
authors.lastname: Tejero
authors.forename: Andrea
authors.initials: A
authors.lastname: Goti
authors.forename: Pedro
authors.initials: P
authors.lastname: Merino
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000470:Alkaloids; D009589:Nitrogen Oxides; D009942:Organometallic Compounds; C015388:nitrones