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

Research output: Contribution to journal › Article › peer-review

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

Access to Document

10.1039/c1sc00116g

Cite this

@article{572fb738851c46deb012267be48ce94d,

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",

month = jul,

doi = "10.1039/c1sc00116g",

language = "English (US)",

volume = "2",

pages = "1258--1261",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "7",

}

TY - JOUR

T1 - Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis

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

Y1 - 2011/7

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=79959456112&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79959456112&partnerID=8YFLogxK

U2 - 10.1039/c1sc00116g

DO - 10.1039/c1sc00116g

M3 - Article

AN - SCOPUS:79959456112

SN - 2041-6520

VL - 2

SP - 1258

EP - 1261

JO - Chemical Science

JF - Chemical Science

IS - 7

ER -

Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this