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

Research output: Contribution to journalArticlepeer-review

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 2011

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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