DIASTEREOSELECTIVE SYNTHESIS OF ENYLMETHYL-1H-IMIDAZOL-4-YL)CYCLOPROPANECARBOXYLIC ACIDS - KEY INTERMEDIATES FOR THE PREPARATION OF POTENT AND CHIRAL HISTAMINE H-3 RECEPTOR AGENTS

Authors
KHAN MA YATES SL TEDFORD CE KIRSCHBAUM K PHILLIPS JG
Citation
Ma. Khan et al., DIASTEREOSELECTIVE SYNTHESIS OF ENYLMETHYL-1H-IMIDAZOL-4-YL)CYCLOPROPANECARBOXYLIC ACIDS - KEY INTERMEDIATES FOR THE PREPARATION OF POTENT AND CHIRAL HISTAMINE H-3 RECEPTOR AGENTS, Bioorganic & medicinal chemistry letters, 7(23), 1997, pp. 3017-3022
Citations number
17
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
7
Issue
23
Year of publication
1997
Pages
3017 - 3022
Database
ISI
SICI code
0960-894X(1997)7:23<3017:DSOE>2.0.ZU;2-O
Abstract
Procedures for the preparation of both enantiomers of nylmethyl-1H-imi dazol-4-yl)-cyclopropanecarboxylic acid are described. The key step in the synthesis is a 3:1 diastereoselective cyclopropanation of rop-2-e noyl)tricyclo[5.2.1.0<1,5>]decane-3,3-dione using trimethylsulfoxonium ylide. These cyclopropanes are useful for the preparation of H-3 rece ptor agents. (C) 1997 Elsevier Science Ltd.