High-pressure Diels-Alder approach to natural kainic acid.
The first Diels-Alder based synthesis of (-)-kainic acid is described. Danishefsky's diene and a vinylogous malonate derived from 4-hydroxyproline combine under high pressure to afford a key bicyclic intermediate with virtually no loss of enantiopurity. This adduct can be converted into the natural product with complete stereocontrol. [reaction: see text].
Pandey
Sushil K
SK
Chimie Recherche (LEDSS), Université Joseph Fourier, 38041 Grenoble, France.
Orellana
Arturo
A
Greene
Andrew E
AE
Poisson
Jean-François
JF
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D006909:Hydroxyproline / Q000737:chemistry; D007202:Indicators and Reagents; D007608:Kainic Acid / Q000138:chemical synthesis*; D008387:Marine Toxins / Q000737:chemistry; D008968:Molecular Conformation; D011312:Pressure; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D008387:Marine Toxins; D006909:Hydroxyproline; D007608:Kainic Acid