R. Scott, B. Golding
Jul 8, 2004
Citations
0
Influential Citations
2
Citations
Journal
Arkivoc
Abstract
A generally applicable synthesis has been developed for 2-substituted oxirane-2-carboxylic esters, which have attracted interest as inhibitors of carnitine palmitoyltransferase-1 (CPT-1) for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). The route involves alkylation of the dianion of 2-methyl-2-propen-1-ol (methallyl alcohol) followed by Sharpless epoxidation. The utility of the method has been demonstrated by the synthesis of (R)-Etomoxir, the best known member of this class of compounds, and ethyl (R)-2-[6-(2,4dinitrophenoxy)hexyl]oxirane-carboxylate, previously synthesised only as a racemate. The high enantiomeric purity of the compounds has been demonstrated by formation of Mosher esters of the products of Sharpless epoxidation and analysis by H NMR spectroscopy.