Stereoselective Total Synthesis of Stereoisomers of Entecavir

Chao Wang; Dong Pei; Li Zhou; Jian Sun

doi:10.1055/a-2069-4552

Synthesis, Table of Contents

Synthesis 2023; 55(19): 3109-3112
DOI: 10.1055/a-2069-4552

paper

Stereoselective Total Synthesis of Stereoisomers of Entecavir

Authors

Chao Wang ∗

^aSchool of Food Science and Bioengineering, Xihua University, Chengdu, 610039, P. R. of China

^bNatural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, P. R. of China
Dong Pei

^cYaoPharma, Co., Ltd., 100 Xingguang Avenue, Renhe Town, Yubei District, Chongqing 401121, P. R. of China
Li Zhou

^bNatural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, P. R. of China
Jian Sun

^bNatural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, P. R. of China

Abstract

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Abstract

Practical methods for the synthesis of three stereoisomers of Entecavir have been developed. Starting from the reported intermediate (1S,2R)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol and (1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol, respectively, three stereoisomers of Entecavir have been prepared with 17–20% overall yields. In principle, other stereoisomers could also be prepared by using the materials and reactions described in this article.

Key words

Entecavir - synthesis - stereoisomers - stereoselective - hepatitis B

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References

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Supplementary Material

Supporting Information (PDF)