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Start Over Author "Kaung KK" Topic bridged bicyclo compounds

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1. Stereoselective syntheses of highly functionalized bicyclo[3.1.0]hexanes: a general methodology for the synthesis of potent and selective mGluR2/3 agonists.

Author

Tan L, Yasuda N, Yoshikawa N, Hartner FW, Eng KK, Leonard WR, Tsay FR, Volante RP, and Tillyer RD

Subjects
Bridged Bicyclo Compounds chemistry, Chromatography, High Pressure Liquid, Hexanes chemistry, Indicators and Reagents, Magnetic Resonance Spectroscopy, Models, Molecular, Molecular Conformation, Stereoisomerism, Bridged Bicyclo Compounds chemical synthesis, Hexanes chemical synthesis, Receptors, Metabotropic Glutamate agonists
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.

Published
2005
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