Citation: Li Wei, Shu Liang, Wang Qiuan, Li Gaoyang, Shan Yang. Synthesis of 8-Prenylflavonoids Natural Products by Microwave Promoted Claisen Rearrangement[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 1976-1982. doi: 10.6023/cjoc201812020 shu

Synthesis of 8-Prenylflavonoids Natural Products by Microwave Promoted Claisen Rearrangement

Li Wei ^a ,
Shu Liang ^a ,
Wang Qiuan ^a,, ,
Li Gaoyang ^b ,
Shan Yang ^b

a.
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
b.
Institution of Agricultural Product Processing, Hunan Academy of Agricultural Science, Changsha 410125

Corresponding author: Wang Qiuan, wangqa@hnu.edu.cn
Received Date: 11 December 2018
Revised Date: 1 March 2019
Available Online: 29 July 2019
Fund Project: Hunan Provincial Natural Science Foundation of China 2018JJ2034Project supported by the Key Laboratory of Hunan Province for Fruit and Vegetable Processing and Quality Safety (No. 2108TP1030) and the Hunan Provincial Natural Science Foundation of China (No. 2018JJ2034)the Key Laboratory of Hunan Province for Fruit and Vegetable Processing and Quality Safety 2108TP1030

Figures(2)

8-Prenylflavonoids are a class natural products with significant biological activities. The total synthesis of three prenylflavonoid natural products, 8-prenylquercetin-3-methylether (1), 8-prenylquerccetin-3, 7, 3', 4'-tetramethyl ether (2) and Artochamin C (3), was achieved through methoxymethyl protection, aldol condensation, iodine catalytic cyclization, dimethyl sulfoxide (DMSO) oxidation, O-prenylation, microwave promoted Claisen rearrangement, deprotection, O-methylation and prenyl group side chain cyclization, staring from commercially available 2, 4, 6-trihydroxyacetophenone and 3, 4-dihydroxy benzaldehyde. The key step of microwave promoted Claisen rearrangement formed 8-C-prenylflavonoids from 5-O- prenylflavonoids was investigated. All the synthesized compounds were confirmed by ¹H NMR、¹³C NMR and MS techniques.
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