Stereocontrolled synthesis of (-)-kainic acid from trans-4-hydroxy-L-proline.
[reaction: see text] A highly stereoselective synthesis of (-)-kainic acid has been achieved in 14 steps and >7% overall yield starting from inexpensive trans-4-hydroxy-L-proline. The key steps are diastereoselective enolate alkylation and cuprate substitution reactions.
Poisson
Jean-François
JF
Chimie Recherche (LEDSS), Université Joseph Fourier, 38041 Grenoble, France jean-francois.poisson@ujf-grenoble.fr
Orellana
Arturo
A
Greene
Andrew E
AE