Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives |
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| Authors: | Yasufumi Ohfune Takashi DemuraSeiji Iwama Hiromi MatsudaKosuke Namba Keiko ShimamotoTetsuro Shinada |
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| Institution: | a Department of Material Science, Graduate School of Science, Osaka City University, Sugimoto, Osaka 558-8585, Japan
b Suntory Institute for Bioorganic Research, Shimamoto-cho, Osaka 618-8503, Japan |
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| Abstract: | Efficient synthesis of (+)-2-aminobicyclo3.1.0]hexane-2,6-dicarboxylic acid (LY354740: 1) and its structurally related analogs (−)-2 and (−)-3 has been accomplished starting with (1S,2R)-1-amino-2-hydroxycyclopentane- or cyclohexanecarboxylic acid (4 or 17 ) via an intramolecular cyclopropanation of α-diazo acetamide. |
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| Keywords: | glutamate analog mGluRs agonist DCG-IV LY354740 l-CCG-III" target="_blank">l-CCG-III transport inhibitor dehydration α-diazo acetamide [2+3] dipolar cycloaddition:cyclopropanation:epimerization |
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