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Synfacts 2009(10): 1072-1072  
DOI: 10.1055/s-0029-1217856
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Azithromycin

Contributor(s): Philip Kocienski, Stewart Eccles
H. C. Kim, S. H. Kang*
Korea Advanced Institute of Science and Technology, Daejeon, Korea
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

Derivatization of erythromycin A led to the formation of azithromycin which is active against a broader range of bacteria, and has greater acid stability and increased oral bioavailability compared with the erythromycins. This ­synthesis stems from the desymmetrization of 2-substituted glycerols to construct the two quaternary stereocenters of azithromycin.