期刊
ORGANIC CHEMISTRY FRONTIERS
卷 6, 期 10, 页码 1603-1607出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9qo00127a
关键词
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资金
- National Nature Science Foundation of China [81760625, 81660576, 81560563]
- Guizhou discipline construction project [GNYL[2017]008]
- Projects of Guizhou province [Qian Ke He Zi [2015]4001, [2015]4032, [2016]5623, [2017]5609, JG[2016]06]
Optically active small molecules based on privileged natural product frameworks and rich in three-dimensional complexity are in high demand. In this context, the merger of two bispirooxindole and hexahydroxanthone cores is a powerful and routine strategy to develop bioactive small molecules. Here, we wish to report the bifunctional oxindole-chromone 4C building block 1 directed asymmetric synthesis of a new class of potential biological structurally bispirooxindole-based hexahydroxant-hones 3 with five adjacent stereocentres, of which two are adjacent spiro quaternary stereocentres. All the products 3 are smoothly obtained with excellent results (up to 91% yield, > 20 : 1 dr and up to > 99% ee). It is noteworthy that such a protocol represents a novel organocatalytic approach for the synthesis of highly desirable but challenging hexahydroxanthone derivatives, which will aid the search for new bioactive molecules.
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