Application of Rhodium-Catalyzed Cyclohydrocarbonylation to the Syntheses of Enantiopure Homokainoids.
Kainic acid, rigidified (S)-glutamic acid, is a well-known kainite receptor agonist for the excitatory transmission in the central nerve system. Our interest in highly selective kainite ligands, prompted us to design a series of new kainic homologues, "homokainoids", i.e., conformationally rigidified (S)-glutamic acids. For the syntheses of enantiopure novel homokainoids (pipecolinoglutamic acids), we successfully applied cyclohydrocarbonylation (CHC) reaction that 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.
Chiou
Wen-Hua
WH
Department of Chemistry, State University of New York at Stony Brook.
Schoenfelder
Angèle
A
Mann
André
A
Ojima
Iwao
I
Acc Chem Res. 2005 May;38(5):404-12
15895978
J Comput Aided Mol Des. 2001 Aug;15(8):753-63
11718479
Science. 1992 Oct 23;258(5082):597-603
1329206
Neuropharmacology. 1998 Oct-Nov;37(10-11):1187-204
9849657
Nature. 1998 Oct 29;395(6705):913-7
9804426
Neuropharmacology. 1995 Jan;34(1):1-26
7623957
Pharmacol Rev. 1989 Jun;41(2):143-210
2558391