title: A straightforward and flexible [4 + 2] route to beta-C-naphthyl-2-deoxy-glycosides through tandem hydroboration-ketal reduction: de novo access to C-naphthyl-6-fluoro and 6,6-difluoro 2-deoxyglycosides.
abstract: [reaction: see text] Under standard hydroboration-oxidation conditions, the dihydropyrans 4 underwent a highly stereocontrolled tandem reaction, involving the expected hydration of the double bond together with the reduction of the ketal moiety. This unprecedented transformation gives rise to a short, [4 + 2]-based synthetic route to (+/-)-beta-C-naphthyl-2-deoxyglycosides 5, which allows a significant structural and functional diversity at C-6. We thus described the first synthesis of (+/-)-C-aryl-6-fluoro and -6,6-difluoro olivosides, via the allylic mono- and difluorides produced by regioselective fluorination of, respectively, hydroxyalkyl and oxoalkyl dihydropyran derivatives.
authors.affiliation: UCO2M, UMR CNRS 6011, Université du Maine, 72085 Le Mans Cedex 9, France.
authors.forename: Quang Vu
authors.initials: QV
authors.lastname: Nguyen
authors.forename: Stéphane
authors.initials: S
authors.lastname: Leconte
authors.forename: Eric
authors.initials: E
authors.lastname: Brown
authors.forename: Danielle
authors.initials: D
authors.lastname: Grée
authors.forename: René
authors.initials: R
authors.lastname: Grée
authors.forename: Gilles
authors.initials: G
authors.lastname: Dujardin
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction
chemical_list: D006027:Glycosides