期刊
CHEMMEDCHEM
卷 3, 期 2, 页码 323-335出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cmdc.200700226
关键词
asymmetric synthesis; dihydroxylation; LY354740; metabotropic glutamate receptors; mGluR2
The asymmetric synthesis and receptor pharmacology of (1S,2R,3R,5R,6S)-2-amino-3-Hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic Acid (+)-9 (HYDIA) and a few of its O-alkylated derivatives are described. The key step of the synthesis utilizes Sharpless' asymmetric dihydroxylation (AD-beta) for the kinetic resolution of a bicyclic racemic precursor olefin. In contrast to the bicyclic glutamate analogue LY354740, which is a potent and selective agonist for the group II metabotropic glutamate receptors (mGluRs), these new conformationally restricted and also hydroxylated or alkoxylated glutamate analogues are potent and selective antagonists for the group II mGIuRs.
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