Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis

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 mc(2)7000 assay. T...

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Published inChemical science (Cambridge) Vol. 2; no. 7; pp. 1258 - 1261
Main Authors Lotesta, Stephen D, Liu, Junjia, Yates, Emma V, Krieger, Inna, Sacchettini, James C, Freundlich, Joel S, Sorensen, Erik J
Format Journal Article
LanguageEnglish
Published England 14.04.2011
Subjects
Antibiotics
Mycobacterium tuberculosis
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Summary: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 mc(2)7000 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.
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ISSN:2041-6520
2041-6539
DOI:10.1039/c1sc00116g