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Synfacts 2012; 8(8): 0815
DOI: 10.1055/s-0032-1316597
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Telithromycin Analogue

Contributor(s):
Philip Kocienski
Li B et al. * Pfizer Global Research and Development, Groton, USA; Shanghai ChemPartner Co. Ltd., Shanghai and Asymchem Life Science Co. Ltd., Tianjin, P. R. of China
Process Development of a Novel Ketolide Antibiotic.

Org. Process Res. Dev. 2012;
16: 788-797
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Further Information

Publication History

Publication Date:
19 July 2012 (online)

 
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Key words

telithromycin analogues - clarithromycin - ketolide antibiotics - Corey–Kim oxidation - reductive amination

Significance

The target telithromycin analogue was under development as an oral antibiotic for the treatment of respiratory infections. The route depicted delivered kilogram quantities of API starting with clarithromycin (A).


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Comment

Note the use of a large-scale Corey–Kim oxidation for the synthesis of the ketolide E. An efficient large-scale synthesis of 3-hydroxy-1,5-naphthyridine-4-carbaldehyde (G) was developed using a Skraup reaction.


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