Novel 3-deoxy-3-descladinosyl-6-O-methyl erythromycin A analogues. Synthesis and in vitro activity.

A series of novel 3-deoxy-3-des-cladinosyl-6-O-methyl erythromycin A analogues has been synthesized and evaluated in vitro for antibacterial activity. These analogues were readily synthesized by tributyltin hydride-mediated radical reduction of a 3-O-xanthyl intermediate to afford the 3-deoxy macrolide. A number of oxime, carbonate, and carbamate derivatives were synthesized and evaluated for antibacterial activity. Overall, these analogues had fairly good antibacterial activity against gram-positive bacteria, although they were generally less potent than the corresponding 3-O-cladinosyl or 3-keto analogues. (C) 1997 Elsevier Science Ltd. All rights reserved.