Synthesis of new bicyclic analogues of glutamic acid

✍ Scribed by Paola Conti; Clelia Dallanoce; Marco De Amici; Carlo De Micheli; Roberta Fruttero

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 649 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00228-8

✦ Synopsis

Regioisomeric 3-hydroxyisoxazolinyl prolines [HIP-A (+)-6 and HIP-B (+)-7], which represent a restricted conformation of NMDA, AMPA, and kainic acid, potent and selective agonists at ionotropic glutamate receptors, have been prepared through two different strategies. In the first approach bromonitrile oxide was added to N-BOC-A3-pyrroline or N-BOC-A3-pyrrolin-2-one and the carboxylic group was subsequently appended. The alternative strategy is based on the cycloaddition of the same 1,3-dipole to N-BOC-3,4-didehydroproline methyl ester.