1. Application of rhodium-catalyzed cyclohydrocarbonylation to the syntheses of enantiopure homokainoids.
- Author
-
Wen-Hua Chiou, Angèle Schoenfelder, André Mann, and Iwao Ojima
- Subjects
- *
CONFERENCES & conventions , *ORGANIC compounds - Abstract
Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194Kainic 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. [ABSTRACT FROM AUTHOR]
- Published
- 2008
- Full Text
- View/download PDF