title: Synthesis and NMR-analysis of tricyclic nucleosides.
abstract: Two anomeric tricyclic nucleosides have been synthesised from diacetone-D-glucose using oxidation, stereoselective Grignard-addition of a vinyl-group, a stereoselective dihydroxylation followed by a tandem ring closing reaction, and finally a nucleobase coupling. The main beta-configured product was examined and its configuration confirmed using NMR-spectroscopy in connection to ab initio calculations. The preferred conformation of this tricyclic nucleoside was described.
authors.affiliation: Department of Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.
authors.forename: P
authors.initials: P
authors.lastname: Nielsen
authors.forename: M
authors.initials: M
authors.lastname: Petersen
authors.forename: J P
authors.initials: JP
authors.lastname: Jacobsen
mesh_terms: D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006844:Hydrocarbons, Cyclic; D009705:Nucleosides