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In recent years, there has been growing interest in ring opening reactions of the macrolide antibiotic erythromycin A leading to the synthesis of chimeric 9aand 8a-azalides1) which are structurally homologous to their potent prototypes azithromycin2,3) and its 8a-isomer4) in their critical eastern halves of the molecule but are functionally simplified in the left-hand part of the 15membered macrocyclic ring. As part of our program in this area we have recently reported the synthesis of 6, 9cyclic seco oxime (2)5) starting from 6, 9-cyclic imino ether (1)6), the key intermediate in the synthesis of azithromycin. Base catalyzed internal acylation of 2 followed by reduction and N-methylation afforded a

Acid Catalyzed Ring Opening Reactions of 6-Deoxy-9-deoxo-9a-aza-9a-homoerythromycin A 6,9-Cyclic Imino Ether.