Optically pure beta-substituted beta-hydroxy aspartates as glutamate transporter blockers.
A short asymmetric synthesis of optically pure beta-substituted beta-hydroxy aspartates is described. The key step is an aldol reaction between a glycine enolate derived from an oxazinone intermediate used as chiral auxiliary and various alpha-keto esters. Excellent diastereomeric excesses are obtained.
Wehbe
Johny
J
UMR 5810-CNRS-LAPP Universités Montpellier I et II, Place E. Bataillon, 34095 Montpellier Cedex, France.
Kassem
Tarek
T
Rolland
Valérie
V
Rolland
Marc
M
Tabcheh
Mohamad
M
Roumestant
Marie-Louise
ML
Martinez
Jean
J
D027322:Amino Acid Transport System X-AG / Q000037:antagonists & inhibitors*; D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D004952:Esters / Q000737:chemistry; D007651:Keto Acids / Q000737:chemistry; D010078:Oxazines / Q000737:chemistry; D013237:Stereoisomerism
D027322:Amino Acid Transport System X-AG; D004952:Esters; D007651:Keto Acids; D010078:Oxazines; D001224:Aspartic Acid