DBU-Catalyzed Inter- and Intramolecular Double Michael Addition of Donor–Acceptor Chromone-Pyrazolone/Benzofuranone Synthons: Access to Spiro-Pyrazolone/Benzofuranone-Hexahydroxanthone Hybrids

Qi Di Wei; Yi-Ming Yao; Shun-Qin Chang; Wu-De Yang; Min-Yi Tian; Xiong-Li Liu; Ying Zhou

doi:10.1055/s-0037-1610728

Synthesis, Table of Contents

Synthesis 2020; 52(01): 85-97
DOI: 10.1055/s-0037-1610728

paper

DBU-Catalyzed Inter- and Intramolecular Double Michael Addition of Donor–Acceptor Chromone-Pyrazolone/Benzofuranone Synthons: Access to Spiro-Pyrazolone/Benzofuranone-Hexahydroxanthone Hybrids

Qi Di Wei §

^aGuizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Yi-Ming Yao §

^aGuizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Shun-Qin Chang

^aGuizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Wu-De Yang

^bCollege of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, Guizhou 550025, P. R. of China

,

Min-Yi Tian

^aGuizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Xiong-Li Liu ∗

^aGuizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, Guizhou University, Guiyang, Guizhou 550025, P. R. of China Email: xlliu1@gzu.edu.cn

,

Ying Zhou

^bCollege of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, Guizhou 550025, P. R. of China

› Author Affiliations

Abstract

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^§ These two authors contributed equally to this work.

Abstract

A DBU-catalyzed inter- and intramolecular double Michael addition of donor–acceptor chromone-pyrazolone/benzofuranone synthons and 3-methyl-4-nitro-5-alkenylisoxazoles has been established, which constructed structurally diverse spiro-pyrazolone/benzofuranone-hexahydroxanthone hybrids bearing five consecutive stereocenters in good yields (up to 91%) with high diastereoselectivities (up to >20:1 dr). Moreover, this strategy further expanded the synthetic potential of bifunctional donor–acceptor chromones, and demonstrated great potential for applications in medicinal chemistry.

Key words

donor–acceptor chromone-pyrazolone synthon - donor–acceptor chromone-benzofuranone synthon - inter- and intramolecular double Michael addition - spiro-pyrazolone-hexahydroxanthone hybrids - spiro-benzofuranone-hexahydroxanthone hybrids

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References

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15 CCDC 1936740 (3r) and 1936741 (5q) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

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