title: A practical and azide-free synthetic approach to oseltamivir from diethyl D-tartrate.
abstract: A short and practical synthesis of oseltamivir was accomplished in 11 steps from inexpensive and abundant diethyl D-tartrate starting material. This azide-free route featured an asymmetric aza-Henry reaction and a domino nitro-Michael/Horner-Wadsworth-Emmons (HWE) reaction as the key steps to construct the relevant cyclohexene ring of the product, which provided an economical and practical alternative for the synthesis of oseltamivir.
authors.affiliation: Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, P. R. China 510006.
authors.forename: Jiang
authors.initials: J
authors.lastname: Weng
authors.forename: Yong-Bo
authors.initials: YB
authors.lastname: Li
authors.forename: Rui-Bin
authors.initials: RB
authors.lastname: Wang
authors.forename: Feng-Quan
authors.initials: FQ
authors.lastname: Li
authors.forename: Can
authors.initials: C
authors.lastname: Liu
authors.forename: Albert S C
authors.initials: AS
authors.lastname: Chan
authors.forename: Gui
authors.initials: G
authors.lastname: Lu
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis*; D003500:Cyclization; D053138:Cyclohexenes / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D006801:Humans; D053124:Influenza A Virus, H5N1 Subtype / Q000201:enzymology; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D053139:Oseltamivir / Q000138:chemical synthesis*; D013644:Tartrates / Q000737:chemistry*
chemical_list: D000998:Antiviral Agents; D053138:Cyclohexenes; D004791:Enzyme Inhibitors; D013644:Tartrates; C052568:cyclohexene; D053139:Oseltamivir; D009439:Neuraminidase; C064501:diethyl tartrate