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

文献类型： 外文期刊

作者： Li Wei 1 ; Su Liang 1 ; Wang Qiu'an 1 ; Li Gaoyang 2 ; Shan Yang 2 ;

作者机构： 1.Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China

2.Hunan Acad Agr Sci, Inst Agr Prod Proc, Changsha 410125, Hunan, Peoples R China

关键词： 8-prenylquercetin-3-methyl ether; 8-prenylquercetin-3,7,3 ',4 '-tetramethyl ether; artochamin C; microwave promoted Claisen rearrangement

期刊名称：CHINESE JOURNAL OF ORGANIC CHEMISTRY （ 影响因子：1.652； 五年影响因子：1.2 ）

ISSN： 0253-2786

年卷期： 2019 年 39 卷 7 期

页码：

收录情况： SCI

摘要： 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 H-1 NMR. C-13 NMR and MS techniques.

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