title: Synthesis of (-)-oseltamivir phosphate (Tamiflu) starting from cis-2,3-bis(hydroxymethyl)aziridine.
abstract: Oseltamivir phosphate (Tamiflu) has been synthesized from cis-2,3-bis(hydroxymethyl)aziridine. After protection of the cis-2,3-bis(hydroxymethyl)aziridine with a Boc group, desymmetrization provided a chiral aziridine, which was a key intermediate to install the required stereogenic center containing a nitrogen atom. Allylation and ring closing metathesis are the key reactions to obtain the cyclic product that was successfully converted to the desired oseltamivir phosphate.
authors.affiliation: Department of Chemistry, Chungbuk National University, Cheongju, Chungbuk 361-763, Korea.
authors.forename: Hong-Se
authors.initials: HS
authors.lastname: Oh
authors.forename: Han-Young
authors.initials: HY
authors.lastname: Kang
mesh_terms: D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D053139:Oseltamivir / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; C578545:cis-2,3-bis(hydroxymethyl)aziridine; D053139:Oseltamivir