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Improved synthesis of enantiomerically pure Etomoxir and its 2,4-dinitrophenyl analogue

Lookup NU author(s): Dr Richard Scott, Professor Bernard Golding

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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-(2,4-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.


Publication metadata

Author(s): Scott R, Golding BT

Publication type: Article

Publication status: Published

Journal: Arkivoc

Year: 2004

Volume: 2004

Issue: x

Pages: 118-133

Date deposited: 07/01/2008

ISSN (print): 1551-7004

ISSN (electronic): 1551-7012

Publisher: Arkat USA, Inc.

URL: http://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/2004/10/

Notes: Commemorative Issue in Honor of Prof. Rodney W. Rickards on the occasion of his 70th birthday


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