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A series of 3-keto-9-O-substituted oxime derivatives of 6-O-methyl erythromycin A were prepared with a novel synthetic route, which include 6 reaction steps--oximation, protection, hydrolysis, oxidation, deprotection and addition. The antibacterial activity of these compounds were tested in vitro against both erythromycin-susceptible and erythromycin-resistant organisms. Several of these derivatives showed improved antibacterial activity against some erythromycin-resistant organisms as compared to erythromycin A.

3-Keto-9-O-substituted Oxime Derivatives of 6-O-Methyl Erythromycin A Synthesis and In Vitro Activity.