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Synthesis 2019; 51(11): 2339-2350
DOI: 10.1055/s-0037-1610875
paper
© Georg Thieme Verlag Stuttgart · New York

Highly Efficient, Catalyst-Free, Diastereoselective, Diversity-Oriented Synthesis of Dihydrocoumarin–Pyrrolidine–Spirooxindoles Bearing Three Contiguous Stereocenters

Xiong Zuo
a   Guizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China   Email: xlliu1@gzu.edu.cn
,
Shuang Chen
a   Guizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China   Email: xlliu1@gzu.edu.cn
,
Sheng-Wen Xu
a   Guizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China   Email: xlliu1@gzu.edu.cn
,
Shun-Qin Chang
a   Guizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China   Email: xlliu1@gzu.edu.cn
,
Xiong-Li Liu  *
a   Guizhou Medicine Edible Plant Resources Application Development Engineering Laboratory, Guizhou University, Guiyang, Guizhou 550025, P. R. of China   Email: xlliu1@gzu.edu.cn
,
Ying Zhou
b   College of Pharmaceutical Sciences, Guizhou University of Chinese Medicine, Guiyang, Guizhou 550025, P. R. of China
,
Wei-Cheng Yuan
c   Key Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China
› Author AffiliationsWe are grateful for the financial support from the National Natural Science Foundation of China (No. 81660576, No. 81560563, No. 81760625) and the Projects of Guizhou Province (Qian Ke He Zi [2016]5623, [2018]5670, [2017]5609 and Qian Jiao Yan He JG Zi [2016]06).
Further Information

Publication History

Received: 21 December 2018

Accepted after revision: 08 March 2019

Publication Date:
03 April 2019 (online)

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Abstract

A new methodology has been developed for the highly efficient diastereoselective construction of dihydrocoumarin–pyrrolidine–spirooxindole collections via a domino Michael/annulation reaction of 3-isothiocyanato oxindoles and coumarins under catalyst-free conditions. The resulting biologically important molecules bearing three pharmacophores and three contiguous stereocenters were obtained in up to 92% yield and >20:1 dr. It is noteworthy that utilization of a carboxylic acid activation/decarboxylation strategy represents an efficient approach for the domino Michael/annulation reaction of the chemically inert coumarin moiety. This protocol could expand candidate libraries, that will benefit the requirement for new bioactive molecules.

Key words

dihydrocoumarins - pyrrolidines - spirooxindoles - 3-isothiocyanato oxindoles - catalyst-free

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610875.
  • Supporting Information
 

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