Efficient short step synthesis of Corey's tamiflu intermediate.
Corey's tamiflu intermediate was synthesized from a bicyclolactam adduct obtained by base-catalyzed Diels-Alder reaction of N-nosyl-3-hydroxy-2-pyridone with ethyl acrylate. A compound that has the same array of functional groups with the Corey's intermediate was obtained in four steps from the DA adduct in 47% overall yield. The intermediate itself was also prepared efficiently by simply changing the protective group.
Kipassa
Nsiama Tienabe
NT
Department of Chemistry and Bioscience, Faculty of Science, Kagoshima University, 1-21-35 Korimoto, Kagoshima 890-0065, Japan.
Okamura
Hiroaki
H
Kina
Kengo
K
Hamada
Toshiyuki
T
Iwagawa
Tetsuo
T
D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors; D053139:Oseltamivir / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D004791:Enzyme Inhibitors; D053139:Oseltamivir; D009439:Neuraminidase