Modification of the macrolide antibiotic midecamycin. III. Formation of neoisomidecamycin.
Treatment of 9-trichloroacetylmidecamycin with aqueous alkali gave an isomer of midecamycin (neoisomidecamycin), in which one double bond underwent allylic rearrangement. The formation of neoisomacrolides was dependent on the nature of protective groups and conditions of deprotective reaction. Treatment of 9-trichloroethoxycarbonylmidecamycin with Zn/acetic acid resulted in no allylic rearrangement.
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D007536:Isomerism; D007933:Leucomycins / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D007933:Leucomycins; C026483:midecamycin