New Bicyclic Azalide Macrolides Obtained by Tandem Palladium Catalyzed Allylic Alkylation/Conjugated Addition Reaction

Unprecedented tandem allylic alkylation/intermolecular Michael addition was used in the preparation of novel bicyclic azalides. NMR spectroscopy was used not only to unambiguously determine and characterize the structures of these unexpected products of chemical reaction but also to investigate the effect the rigid bicyclic modification has on the conformation of the whole molecule. Thus, some of the macrolides prepared showed antibacterial activity in the range of well-known antibiotic drug azithromycin.

Automated summary

This study utilized an unprecedented tandem reaction to prepare novel bicyclic azalides, and NMR spectroscopy was used to determine the structure and investigate the effect of the rigid bicyclic modification on the molecule's conformation. Some prepared compounds exhibited antibacterial activity similar to azithromycin.