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Lookup NU author(s): Dr Richard Scott,
Emeritus Professor Bernard Golding
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-(2,4-dinitrophenoxy)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 1H NMR spectroscopy.
Author(s): Scott R, Golding BT
Publication type: Article
Publication status: Published
Date deposited: 07/01/2008
ISSN (print): 1551-7004
ISSN (electronic): 1551-7012
Publisher: Arkat USA, Inc.
Notes: Commemorative Issue in Honor of Prof. Rodney W. Rickards on the occasion of his 70th birthday