Affiliation:
1. 1Faculty of Pharmacy, Université Louis Pasteur Strasbourg, France
2. 2Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York, USA
Abstract
Kainic acid (KA), rigidified (S)-glutamic acid, is a well-known kainite receptor agonist for excitatory transmission in the central nervous system (CNS). Our interest in highly selective kainite ligands prompted us to design a series of new kainic homologs, "homokainoids", i.e., conformationally rigidified (S)-glutamic acids. For the syntheses of enantiopure novel homokainoids (pipecolino-glutamic acids), we successfully applied the cyclohydrocarbonylation (CHC) reaction, which has been developed in these laboratories. Efficient total syntheses of enantiopure novel homokainoids from (R)-serine feature the highly diastereoselective conjugate addition and the regioselective CHC process in the key steps.
Subject
General Chemical Engineering,General Chemistry
Cited by
8 articles.
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