title: Intramolecular oxyselenation of (5'S)-C-(4-phenyl-1,3-butadienyl)uridine: synthesis of octosyl nucleosides.
abstract: (5'S)-C-(4-Phenyl-1,3-butadienyl)uridine (8) was prepared from the (5'S)-C-styryl derivative 2. Intramolecular oxyselenation of 8 proceeded in a 6-endo-trig manner to yield the cyclized product 9. Compound 9, having appropriate substituents at the 5'-, 6'-, and 7'-positions, was found to serve as a key intermediate for the synthesis of octosyl nucleosides.
authors.affiliation: School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Haraguchi
authors.forename: M
authors.initials: M
authors.lastname: Hosoe
authors.forename: H
authors.initials: H
authors.lastname: Tanaka
authors.forename: S
authors.initials: S
authors.lastname: Tsuruoka
authors.forename: K
authors.initials: K
authors.lastname: Kanmuri
authors.forename: T
authors.initials: T
authors.lastname: Miyasaka
mesh_terms: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000737:chemistry; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives*
chemical_list: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; C113078:C-(4-phenyl-1,3-butadienyl)uridine; D007202:Indicators and Reagents; D009705:Nucleosides; C011952:nikkomycin; D014529:Uridine