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Synthesis 2020; 52(01): 85-97
DOI: 10.1055/s-0037-1610728
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
Authors
This work received financial support from National Nature Science Foundation of China (81760625, 81660576 and 81560563) and Projects of Guizhou Province ([2016]5623, JG[2016]06, [2019]1402, [2017]5609 and [2018]5781).
Further Information
Publication History
Received: 27 June 2019
Accepted after revision: 18 August 2019
Publication Date:
13 September 2019 (online)
§ 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 hybridsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610728.
- Supporting Information (PDF)
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