Synthesis of 4'-deoxy-4'-fluorokanamycin A and B.
4'-Deoxy-4'-fluorokanamycins A (17) and B (25) have been prepared through fluorinative ring-opening of the D-galacto-3',4'-oxiranes (8 and 21) derived from kanamycin A and B with potassium hydrogenfluoride in ethane-1,2-diol. The mechanism of preponderant formation of the 4'-deoxy-4'-fluoro-D-gluco (9 and 22) over the 3'-deoxy-3'-fluoro-D-gulo derivatives was discussed. In the synthesis of 25, the unusual 3',6'-epimine (23) was the main product along with the 4'-deoxy-4'-fluoro derivative. The mechanism of this reaction is also discussed. Both 17 and 25 were active against resistant bacteria producing aminoglycoside-adenylylating enzymes for HO-4'.
Takahashi
Y
Y
Institute of Bioorganic Chemistry, Kawasaki, Japan.
Tsuneda
S
S
Tsuchiya
T
T
Koyama
Y
Y
Umezawa
S
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002240:Carbohydrate Sequence; D007612:Kanamycin / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data
D000900:Anti-Bacterial Agents; D007612:Kanamycin