Highlights of Semi-synthetic Developments from Erythromycin A

Author: Wu, Y-J.

Source: Current Pharmaceutical Design, Volume 6, Number 2, 1 January 2000 , pp. 181-223(43)

Publisher: Bentham Science Publishers

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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