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Issue 7, 2011
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Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis

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Abstract

New pleuromutilin-like compounds were synthesized in approximately 11 steps from 3-allylcyclopent-2-enone by a strategy featuring sequential carbonyl addition reactions. Several analogs possessing the C14 tiamulin ester side chain displayed activity in a Mycobacterium tuberculosis mc27000 assay. The results described herein provide a basis for further efforts to expand the structural and stereochemical diversity of the pleuromutilin class of bacterial protein synthesis inhibitors through advances in chemical synthesis.

Graphical abstract: Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis

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Publication details

The article was received on 28 Feb 2011, accepted on 22 Mar 2011 and first published on 14 Apr 2011


Article type: Edge Article
DOI: 10.1039/C1SC00116G
Citation: Chem. Sci., 2011,2, 1258-1261
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    Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis

    S. D. Lotesta, J. Liu, E. V. Yates, I. Krieger, J. C. Sacchettini, J. S. Freundlich and E. J. Sorensen, Chem. Sci., 2011, 2, 1258
    DOI: 10.1039/C1SC00116G

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