A practical and azide-free synthetic approach to oseltamivir from diethyl D-tartrate.
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.
Weng
Jiang
J
Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, P. R. China 510006.
Li
Yong-Bo
YB
Wang
Rui-Bin
RB
Li
Feng-Quan
FQ
Liu
Can
C
Chan
Albert S C
AS
Lu
Gui
G
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*
D000998:Antiviral Agents; D053138:Cyclohexenes; D004791:Enzyme Inhibitors; D013644:Tartrates; C052568:cyclohexene; D053139:Oseltamivir; D009439:Neuraminidase; C064501:diethyl tartrate