Synthesis 2020; 52(10): 1576-1584
DOI: 10.1055/s-0039-1691699
paper
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Total Synthesis of Arundinolides A and B

Caizhu Chang
a   State 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
b   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   Email: dzb04982@wit.edu.cn
,
Jialin Geng
a   State 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
c   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Yinxin Liu
a   State 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
c   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Yuguo Du
a   State 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
c   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Jun Liu
a   State 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
c   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Zhi-Bing Dong
a   State 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
b   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   Email: dzb04982@wit.edu.cn
› Author Affiliations
We thank the foundation support from the National Key Research and Development Program of China (2016YFA0203102), the Strategic Priority Research Program of Chinese Academy of Sciences (Grant XDB14040201), National Natural Science Foundation of China (Projects 21302150 and 21602082), Science and Technology Department of Hubei Province (2019CFB596), Chen-Guang program from Hubei Association for Science and Technology, Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University (KLSAOFM1810), Key Laboratory of Hubei­ Province for Coal Conversion and New Carbon Materials, Wuhan­ University of Science and Technology (WKDM202003).
Further Information

Publication History

Received: 07 December 2019

Accepted after revision: 09 January 2020

Publication Date:
05 February 2020 (online)


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.

Supporting Information

 
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