Citation: Ji Yu, Yao Hui, Liu Yi, Huang Nianyu, Liu Mingguo. Synthesis and Cytotoxic Activity of C-Vinyl-rhamnopyranoside Derivatives[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 2051-2061. doi: 10.6023/cjoc202003037 shu

Synthesis and Cytotoxic Activity of C-Vinyl-rhamnopyranoside Derivatives

Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002

Corresponding author: Huang Nianyu, hny115@126.com Liu Mingguo, mgliu1966@163.com
Received Date: 14 March 2020
Revised Date: 19 April 2020
Available Online: 23 April 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21602123), and the Youth Talent Development Foundation and Scientific Foundation from Graduate School of China Three Gorges University (No. SDYC2016121)the National Natural Science Foundation of China 21602123the Youth Talent Development Foundation and Scientific Foundation from Graduate School of China Three Gorges University SDYC2016121

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A novel gold(Ⅰ)-catalyzed glycosylation method was described to synthesize C-vinyl-rhamnopyranoside derivatives using stable propargylic carboxylates and 3, 4-di-O-acetyl-L-rhamnal as starting materials, based on the tandem intermolecular 1, 3-acyloxy migration/Ferrier rearrangement. The C-glycosylation process has been verified by O¹⁸ isotopic labeling experiment, and the absolute configuration of synthesized products was determined by X-ray single crystal diffraction. The cytotoxic activity was investigated by methyl thiazolyl tetrazolium (MTT). It indicates that product 3i has strong inhibitory effect on human gastric cancer cells HGC-27 with IC₅₀ 18.29 μmol·L^-1. The described synthetic method was outstanding with easy-to-operate, high diastereoselectivity, and mild reaction condition.
- Ferrier rearrangement,
- rhamnopyranoside,
- cytotoxic activity,
- diastereoselectivity
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