Stereoselective Syntheses of Highly Functionalized Bicyclo[3.1.0]hexanes:  A General Methodology for the Synthesis of Potent and Selective mGluR2/3 Agonists

Stereoselective Syntheses of Highly Functionalized Bicyclo[3.1.0]hexanes:  A General Methodology for the Synthesis of Potent and Selective mGluR2/3 Agonists

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...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 70; no. 20; pp. 8027 - 8034
Main Authors: Tan, Lushi, Yasuda, Nobuyoshi, Yoshikawa, Naoki, Hartner, Frederick W, Eng, Kan Kaung, Leonard, William R, Tsay, Fuh-Rong, Volante, Ralph P, Tillyer, Richard D
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 30-09-2005
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Chemistry
Chromatography, High Pressure Liquid
Exact sciences and technology
Hexanes - chemical synthesis
Hexanes - chemistry
Indicators and Reagents
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Organic chemistry
Preparations and properties
Receptors, Metabotropic Glutamate - agonists
Stereoisomerism
Cyclopropanation
Stereoselectivity
Agonist
Diol
Functionalization
Epoxide
Bicyclic compound
Selectivity
Chemical synthesis
mglu2 glutamate receptor
mglu3 glutamate receptor
Ring cleavage
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Description
Summary: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.
Bibliography:istex:49C683B5046BE2CF381A60996B1CF82FB6FE8D93
ark:/67375/TPS-JPFQ7H60-F
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0511187