title: Development of a concise synthesis of (-)-oseltamivir (Tamiflu).
abstract: We report a full account of our work towards the development of an eight-step synthesis of anti-influenza drug (-)-oseltamivir (Tamiflu) from commercially available starting materials. The final synthetic route proceeds with an overall yield of 30 %. Key transformations include a novel palladium-catalyzed asymmetric allylic alkylation reaction (Pd-AAA) as well as a rhodium-catalyzed chemo-, regio-, and stereoselective aziridination reaction.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Ting
authors.initials: T
authors.lastname: Zhang
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D006801:Humans; D007251:Influenza, Human / Q000188:drug therapy; D053139:Oseltamivir / Q000138:chemical synthesis* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000998:Antiviral Agents; D053139:Oseltamivir; D010165:Palladium