title: Time Economical Total Synthesis of (-)-Oseltamivir.
abstract: A time economical 60 min total synthesis of (-)-oseltamivir was accomplished in a single reaction vessel over five steps. One of the key issues is reduction in the number of steps by eliminating lengthy reaction steps with substitution of a rapid epimerization step. A catalytic system consisting of three reagents, namely, diphenylprolinol silyl ether, thiourea, and acid, was developed for a rapid asymmetric Michael reaction with excellent diastereo- and enantioselectivities. All reactions were optimized in terms of not only yield and selectivity but also reaction time.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University , 6-3 Aramaki-Aza Aoba-ku, Sendai, Miyagi 980-8578, Japan.
authors.forename: Yujiro
authors.initials: Y
authors.lastname: Hayashi
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University , 6-3 Aramaki-Aza Aoba-ku, Sendai, Miyagi 980-8578, Japan.
authors.forename: Shin
authors.initials: S
authors.lastname: Ogasawara
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis*; D002384:Catalysis; D004526:Efficiency; D004987:Ethers / Q000737:chemistry; D005561:Formates; D053139:Oseltamivir / Q000138:chemical synthesis*; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D004987:Ethers; D005561:Formates; C529940:diphenylprolinol silyl ether; C030544:formic acid; D053139:Oseltamivir; D011392:Proline; D013890:Thiourea