title: Synthesis of the anti-influenza agent (-)-oseltamivir free base and (-)-methyl 3-epi-shikimate.
abstract: A new enantioselective synthesis of the anti-influenza agent (-)-oseltamivir free base (7.1% overall yield; 98% ee) and (-)-methyl 3-epi-shikimate (16% overall yield; 98% ee) has been described from readily available raw materials. Sharpless asymmetric epoxidation and diastereoselective Barbier allylation of an aldehyde are the key reactions employed in the incorporation of chirality, while the cyclohexene carboxylic ester core was constructed through a ring closing metathesis reaction.
authors.affiliation: Chemical Engineering and Process Development Division, National Chemical Laboratoty, Pashan Road, Pune 411008, India.
authors.forename: Varun
authors.initials: V
authors.lastname: Rawat
authors.forename: Soumen
authors.initials: S
authors.lastname: Dey
authors.forename: Arumugam
authors.initials: A
authors.lastname: Sudalai
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis*; D002384:Catalysis; D006865:Hydrogenation; D015394:Molecular Structure; D053139:Oseltamivir / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D000998:Antiviral Agents; C453473:methyl shikimate; D053139:Oseltamivir; D012765:Shikimic Acid