Journal of Organic Chemistry 2010-05-07

A practical and azide-free synthetic approach to oseltamivir from diethyl D-tartrate.

Jiang Weng, Yong-Bo Li, Rui-Bin Wang, Feng-Quan Li, Can Liu, Albert S C Chan, Gui Lu

Index: J. Org. Chem. 75(9) , 3125-8, (2010)

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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.