Issue 7, 2011
From the journal:

Chemical Science

Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis†

Stephen D. Lotesta,a   Junjia Liu,a   Emma V. Yates,a   Inna Krieger,b   James C. Sacchettini,b   Joel S. Freundlichb  and  Erik J. Sorensen*a  

* Corresponding authors

a Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, New Jersey, USA
E-mail: ejs@princeton.edu
Fax: +1-608-258-1980
Tel: +1-609-258-8135

b Department of Biochemistry and Biophysics, Texas A&M University, College Station, Texas, USA

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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Article information

DOI
https://doi.org/10.1039/C1SC00116G
Article type
Edge Article
Submitted
28 Feb 2011
Accepted
22 Mar 2011
First published
14 Apr 2011

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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