Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis

Stephen D. Lotesta, Junjia Liu, Emma V. Yates, Inna Krieger, James C. Sacchettini, Joel S. Freundlich, Erik J. Sorensen

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21 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1258-1261
Number of pages4
JournalChemical Science
Volume2
Issue number7
DOIs
StatePublished - Jul 1 2011
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Lotesta, S. D., Liu, J., Yates, E. V., Krieger, I., Sacchettini, J. C., Freundlich, J. S., & Sorensen, E. J. (2011). Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis. Chemical Science, 2(7), 1258-1261. https://doi.org/10.1039/c1sc00116g