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A bifunctional pyrazolone–chromone synthon directed organocatalytic double Michael cascade reaction: forging five stereocenters in structurally diverse hexahydroxanthones

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Abstract

The merging of two or more known natural product-based scaffolds is a powerful and routine strategy to develop bioactive small molecules. Here, we wish to report the first example of the bifunctional pyrazolone–chromone synthon 1 directed organocatalytic double Michael tandem reaction, which serves as a fruitful strategy for the facile access to structurally diverse hexahydroxanthone derivatives 3 and 5 bearing five continuous stereocenters, including two all-carbon quaternary spiro-stereocenters. These products were smoothly afforded in up to 87% yield, >20 : 1 dr and >99% ee under mild conditions. This is also the first example of catalytic enantioselective access to spirocyclohexanebenzofuranones and bispirocarbocyclic pyrazolones, potentially useful in medicinal chemistry.

Graphical abstract: A bifunctional pyrazolone–chromone synthon directed organocatalytic double Michael cascade reaction: forging five stereocenters in structurally diverse hexahydroxanthones

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Publication details

The article was received on 19 Feb 2019, accepted on 11 Mar 2019 and first published on 26 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00265K
Citation: Org. Chem. Front., 2019, Advance Article

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    A bifunctional pyrazolone–chromone synthon directed organocatalytic double Michael cascade reaction: forging five stereocenters in structurally diverse hexahydroxanthones

    X. Liu, X. Zuo, J. Wang, S. Chang, Q. Wei and Y. Zhou, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00265K

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