Stereoselective Total Synthesis of Arundinolides A and B

Caizhu Chang; Jialin Geng; Yinxin Liu; Yuguo Du; Jun Liu; Zhi-Bing Dong

doi:10.1055/s-0039-1691699

Synthesis, Table of Contents

Synthesis 2020; 52(10): 1576-1584
DOI: 10.1055/s-0039-1691699

paper

Stereoselective Total Synthesis of Arundinolides A and B

Caizhu Chang

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China Email: junliu@rcees.ac.cn

^bSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China Email: dzb04982@wit.edu.cn

,

Jialin Geng

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China Email: junliu@rcees.ac.cn

^cSchool of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Yinxin Liu

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China Email: junliu@rcees.ac.cn

^cSchool of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Yuguo Du

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China Email: junliu@rcees.ac.cn

^cSchool of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Jun Liu ∗

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China Email: junliu@rcees.ac.cn

^cSchool of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Zhi-Bing Dong ∗

^aState Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China Email: junliu@rcees.ac.cn

^bSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China Email: dzb04982@wit.edu.cn

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Abstract

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Abstract

The efficient and enantioselective syntheses of arundinolides A and B have been accomplished for the first time from chiral pool methyl-2,3-O-isopropylidene-β-d-ribofuranoside and d-ethyl lactate. The key features of the total synthesis are intramolecular crotonyl migration and NaBH₄-CuCl catalyzed regioselective reduction and cross-metathesis reaction.

Key words

arundinolides - total synthesis - chiral pool - regioselective reduction - crotonyl migration

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References

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