Highlights of Semi-synthetic Developments from Erythromycin A

Yong-Jin      Wu

doi:10.2174/1381612003401316

Abstract

Earlier semi-synthetic studies of erythromycin A culminated in the discovery of two successful second generation macrolide antibiotics, azithromycin and clarithromycin, for the treatment of community-acquired bacterial infections. More recent structural modifications of erythromycin A have resulted in the discovery of novel ketolide antibiotics and new motilide prokinetic agents. This review is an account of the semi-synthetic developments from erythromycin A by chemical transformations.

Keywords: erythromycin A, Clarithormycin, macrolide antibiotics azithromycin, community acquired bacterial infection, prokinetic agnets, saccharoployspora erythaeas, chlamydia, legionella, azithromycin, isomerization, oxime, beckmann rearrangement, 9Z oxime, 9E oxime, transannular lactamization, ring contraction, translactonization, DAST induced ring contraction, Ring opening, trimethylsilanolate KOTMS, interamolecular michael addition, olefin metaathesis, nucleophilic substitution, Interamolecular heck reaction, 3 6 ethers, cyclic aminals, N ketals