title: Efficient short step synthesis of Corey's tamiflu intermediate.
abstract: 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.
authors.affiliation: Department of Chemistry and Bioscience, Faculty of Science, Kagoshima University, 1-21-35 Korimoto, Kagoshima 890-0065, Japan.
authors.forename: Nsiama Tienabe
authors.initials: NT
authors.lastname: Kipassa
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Okamura
authors.forename: Kengo
authors.initials: K
authors.lastname: Kina
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Hamada
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Iwagawa
mesh_terms: 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
chemical_list: D004791:Enzyme Inhibitors; D053139:Oseltamivir; D009439:Neuraminidase