Efficient total synthesis of (-)-kaitocephalin.
A highly diastereoselective total synthesis of (-)-kaitocephalin, a novel antagonist of ionotropic glutamate receptors, was accomplished in 12 steps starting from 5-substituted proline ester via the aldol reaction with OBO-serine aldehyde, (E)-selective alpha,beta-dehydroamino acid synthesis using a new HWE reagent, and catalytic hydrogenation.
Hamada
Makoto
M
Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan.
Shinada
Tetsuro
T
Ohfune
Yasufumi
Y
D002384:Catalysis; D005998:Glycine / Q000737:chemistry; D006865:Hydrogenation; D007202:Indicators and Reagents / Q000737:chemistry; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007202:Indicators and Reagents; D011758:Pyrroles; C442421:kaitocephalin; D005998:Glycine