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

文献情報

出版日 2019-03-26

DOI 10.1039/C9QO00265K

インパクトファクター 5.281

著者

Xiong Zuo, Jun-Xin Wang, Shun-qin Chang, Qi-Di Wei, Ying Zhou

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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