title: Stereoselective synthesis of (+)-1-deoxyaltronojirimycin.
abstract: A stereocontrolled, facile and high-yield approach for producing (+)-altroDNJ, has been developed starting from the inexpensive commercial cis 2-butene-1,4-diol. Sharpless epoxidation and a subsequent dihydroxylation were used for the introduction of all stereocentres; finally, the ring closure under basic conditions afforded the piperidine heterocycle.
authors.affiliation: a Department of Chemistry, CNR-IBPM , Sapienza University of Rome , Rome , Italy.
authors.forename: Giuliana
authors.initials: G
authors.lastname: Righi
authors.affiliation: b Department of Chemistry , Sapienza University of Rome , Rome , Italy.
authors.forename: Emanuela
authors.initials: E
authors.lastname: Mandic'
authors.affiliation: b Department of Chemistry , Sapienza University of Rome , Rome , Italy.
authors.forename: Ilaria
authors.initials: I
authors.lastname: Tirotta
authors.affiliation: b Department of Chemistry , Sapienza University of Rome , Rome , Italy.
authors.forename: Gaia Clara Mercedes
authors.initials: GC
authors.lastname: Naponiello
authors.affiliation: b Department of Chemistry , Sapienza University of Rome , Rome , Italy.
authors.forename: Carla
authors.initials: C
authors.lastname: Sappino
authors.affiliation: b Department of Chemistry , Sapienza University of Rome , Rome , Italy.
authors.forename: Cristina
authors.initials: C
authors.lastname: Marucci
authors.affiliation: b Department of Chemistry , Sapienza University of Rome , Rome , Italy.
authors.forename: Michela
authors.initials: M
authors.lastname: Tomei
authors.affiliation: a Department of Chemistry, CNR-IBPM , Sapienza University of Rome , Rome , Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Bovicelli
mesh_terms: D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis; D006571:Heterocyclic Compounds; D006900:Hydroxylation; D007202:Indicators and Reagents; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; C553837:L-altro-1-deoxynojirimycin; D017485:1-Deoxynojirimycin
keywords: 1-deoxyaltronojirimycin; Iminosugar; dihydroxylation; heterocycles; stereoselective synthesis