Syntheses of 9-substituted josamycin, 13-substituted isojosamycin and their tetrahydro derivatives.
Derivatives of josamycin and isojosamycin modified at C-9 and C-13 have been prepared by reaction sequences involving treatment of josamycin with alcohols, phenol or 1-methyl-1H-tetrazol-5-ylthiol in acidic media. Several tetrahydro derivatives of josamycin and isojosamycin have also been prepared by reaction sequences involving catalytic hydrogenation. From the 1H NMR studies, it was found that the conformation of the macro-lactone portion of 13-O-methylisojosamycin dimethylacetal, a key intermediate, is flexible and changeable with variation of the solvent.
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D007933:Leucomycins / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy
D000900:Anti-Bacterial Agents; D007933:Leucomycins