Publications [#340430] of Eric J. Toone

Journal Articles

1. Liang, X; Gopalaswamy, R; Navas, F; Toone, EJ; Zhou, P, A Scalable Synthesis of the Difluoromethyl-allo-threonyl Hydroxamate-Based LpxC Inhibitor LPC-058., J Org Chem, vol. 81 no. 10 (May, 2016), pp. 4393-4398 [doi]
   (last updated on 2026/01/15)

   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.