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Synlett 2019; 30(06): 748-752
DOI: 10.1055/s-0037-1612215
letter
© Georg Thieme Verlag Stuttgart · New York

A New Formal Synthetic Route to Entecavir

Lixia Liu
a   School of Life Science, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China
,
Yongli Sun
a   School of Life Science, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China
,
Jiwu Wang
b   School of Pharmacy, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China
,
Wentao Ou
a   School of Life Science, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China
,
Xiaoji Wang*
a   School of Life Science, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China
,
Shuangping Huang*
b   School of Pharmacy, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China
c   College of Biomedical Engineering, Taiyuan University of Technology, 030024 Taiyuan, Shanxi, P. R. of China   Email: 2012207455@tju.edu.cn
› Author Affiliations
This work was financially supported by the National Science Foundation of China (21062088, 21562020) and the Science and Technology Plan Project of Jiangxi Province (No. 20151BBG70028, 20142BBE50006).
Further Information

Publication History

Received: 21 December 2018

Accepted after revision: 20 January 2019

Publication Date:
06 March 2019 (online)

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Abstract

We describe a new and straightforward approach to the formal synthesis of the hepatitis B virus inhibitor entecavir, an important hepatitis B drug, in ten steps overall. Key features of the route are a Morita–Baylis–Hillman reaction, a Sharpless asymmetric epoxidation, a reductive epoxide opening of an α,β-epoxy ketone, and a Riley selenium dioxide oxidation.

Key words

entecavir - formal synthesis - epoxy ketones - Sharpless epoxidation - ring cleavage - Riley oxidation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612215.
  • Supporting Information
 

  • References and Notes

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