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J Org Chem ; 70(20): 8027-34, 2005 Sep 30.
Article in English | MEDLINE | ID: mdl-16277324

ABSTRACT

[Chemical reaction: See text] A Et3Al mediated intramolecular epoxide opening, cyclopropanation reaction is described. The transformation provided highly functionalized bicyclo[3.1.0]hexane systems in high efficiency and with perfect H or F endo selectivity. Application of this reaction to the synthesis of mGluR2/3 agonist 1 (43% overall yield) and a few intermediates suitable for the synthesis of other bicyclo[3.1.0]hexane mGluR2/3 agonists is discussed.


Subject(s)
Bridged Bicyclo Compounds/chemical synthesis , Hexanes/chemical synthesis , Receptors, Metabotropic Glutamate/agonists , Bridged Bicyclo Compounds/chemistry , Chromatography, High Pressure Liquid , Hexanes/chemistry , Indicators and Reagents , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular Conformation , Stereoisomerism
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