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

doi:10.1039/c1sc00116g

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

Chemistry

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25 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 language	English (US)
Pages (from-to)	1258-1261
Number of pages	4
Journal	Chemical Science
Volume	2
Issue number	7
DOIs	https://doi.org/10.1039/c1sc00116g
State	Published - Jul 2011

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1039/c1sc00116g

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title = "Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis",

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.",

author = "Lotesta, \{Stephen D.\} and Junjia Liu and Yates, \{Emma V.\} and Inna Krieger and Sacchettini, \{James C.\} and Freundlich, \{Joel S.\} and Sorensen, \{Erik J.\}",

year = "2011",

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AU - Lotesta, Stephen D.

AU - Liu, Junjia

AU - Yates, Emma V.

AU - Krieger, Inna

AU - Sacchettini, James C.

AU - Freundlich, Joel S.

AU - Sorensen, Erik J.

PY - 2011/7

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AB - 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.

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Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis

Abstract

All Science Journal Classification (ASJC) codes

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