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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1019-1024

Application of rhodium-catalyzed cyclohydrocarbonylation to the syntheses of enantiopure homokainoids

Wen-Hua Chiou, Angèle Schoenfelder1, André Mann1 and Iwao Ojima2

1 Faculty of Pharmacy, Université Louis Pasteur Strasbourg, France
2 Department 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.