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

doi:10.1021/jo100187m

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^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

68 Scopus citations

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.

Original language	English
Pages (from-to)	3125-3128
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	75
Issue number	9
DOIs	https://doi.org/10.1021/jo100187m
State	Published - 7 May 2010
Externally published	Yes

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10.1021/jo100187m

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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.",

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AU - Weng, Jiang

AU - Li, Yong Bo

AU - Wang, Rui Bin

AU - Li, Feng Quan

AU - Liu, Can

AU - Chan, Albert S.C.

AU - Lu, Gui

PY - 2010/5/7

Y1 - 2010/5/7

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AB - 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.

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IS - 9

ER -

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

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