Anthrone C-glycosides are an interesting class of natural products in which the carbohydrate is connected at the C-10 position of the anthrone through a C-C bond linkage. This class of natural products was found to exhibit cytotoxicity against various tumor cell lines, such as human breast cancer and non-small cell lung cancer. The synthesis of a model anthrone C-glycoside was achieved in 10 steps from dihydroxyanthracenone and a C1-halosugar. Key steps in the synthesis include a SN<sub>2</sub>-type β-glycosylation, Kochi decarboxylation, and PhSK deprotection of aromatic pivalate protecting group.

Synthesis of a model anthrone C-glycoside

256th National Meeting (2018)

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