title: Synthesis of 5-deoxy-5-fluoro- and 5-deoxy-5,5-difluoro-netilmicin.
abstract: 5-Deoxy-5-fluoro- (9) and 5-deoxy-5,5-difluoro-netilmicin (27) have been prepared from the corresponding 5-epi and 5-oxo derivatives of netilmicin by treatment with DAST. Structures of the fluorinated by-products (10, 11, and 12) obtained in one of the synthesis of 9 were determined. 5-Epi-netilmicin (13) and 5-epi-6'-N-methyl-netilmicin (21) have also been prepared.
authors.affiliation: Institute of Bioorganic Chemistry, Kawasaki, Japan.
authors.forename: E
authors.initials: E
authors.lastname: Umemura
authors.forename: T
authors.initials: T
authors.lastname: Tsuchiya
authors.forename: Y
authors.initials: Y
authors.lastname: Koyama
authors.forename: S
authors.initials: S
authors.lastname: Umezawa
mesh_terms: D000818:Animals; D002240:Carbohydrate Sequence; D004305:Dose-Response Relationship, Drug; D007928:Lethal Dose 50; D051379:Mice; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D009428:Netilmicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000633:toxicity
chemical_list: D009428:Netilmicin