title: Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation.
abstract: Calystegine A(3) is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-d-glucose applying a diastereoselective allylation protocol.
authors.affiliation: Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
authors.forename: Tina Secher
authors.initials: TS
authors.lastname: Rasmussen
authors.forename: Henrik Helligsø
authors.initials: HH
authors.lastname: Jensen
mesh_terms: D000478:Alkylation; D003847:Deoxyglucose / Q000737:chemistry*; D008968:Molecular Conformation; D009662:Nortropanes / Q000138:chemical synthesis* / Q000737:chemistry; D012991:Solanaceous Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009662:Nortropanes; D012991:Solanaceous Alkaloids; C110568:calystegine A3; D003847:Deoxyglucose