A Scalable Synthesis of the Difluoromethyl-allo-threonyl Hydroxamate-Based LpxC Inhibitor LPC-058.
Published
Journal Article
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.
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Duke Authors
Cited Authors
- Liang, X; Gopalaswamy, R; Navas, F; Toone, EJ; Zhou, P
Published Date
- May 20, 2016
Published In
Volume / Issue
- 81 / 10
Start / End Page
- 4393 - 4398
PubMed ID
- 27128325
Pubmed Central ID
- 27128325
Electronic International Standard Serial Number (EISSN)
- 1520-6904
Digital Object Identifier (DOI)
- 10.1021/acs.joc.6b00589
Language
- eng
Conference Location
- United States