Synthesis of 5-deoxy-5-fluoro- and 5-deoxy-5,5-difluoro-netilmicin.
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.
Umemura
E
E
Institute of Bioorganic Chemistry, Kawasaki, Japan.
Tsuchiya
T
T
Koyama
Y
Y
Umezawa
S
S
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
D009428:Netilmicin