| Literature DB >> 27128325 |
Xiaofei Liang1, Ramesh Gopalaswamy1, Frank Navas1, Eric J Toone1,2, Pei Zhou1,2.
Abstract
The difluoromethyl-allo-threonyl hydroxamate-based compound LPC-058 is a potent inhibitor of UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase (LpxC) in Gram-negative bacteria. A scalable synthesis of this compound is described. The key step in the synthetic sequence is a transition metal/base-catalyzed aldol reaction of methyl isocyanoacetate and difluoroacetone, giving rise to 4-(methoxycarbonyl)-5,5-disubstituted 2-oxazoline. A simple NMR-based determination of enantiomeric purity is also described.Entities:
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Year: 2016 PMID： 27128325 PMCID： PMC5164921 DOI： 10.1021/acs.joc.6b00589
Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354