摘要/Abstract

8-异戊烯基黄酮是一类具有显著生物活性的天然产物.以2，4，6-三羟基苯乙酮和3，4-二羟基苯甲醛为原料，用氯甲基甲醚保护羟基，经羟醛缩合、碘催化环合、过氧丙酮（DMDO）氧化、O-异戊烯基化、微波促进的Claisen重排、脱甲氧甲基保护基、O-甲基化和异戊烯基侧链环合等反应步骤，完成了8-异戊烯基槲皮素-3-甲醚（1）、8-异戊烯基槲皮素-3，7，3'，4'-四甲醚（2）和Artochamin C（3）这3种8-异戊烯基黄酮类天然产物的合成.并对由微波促进的由5-O-异戊烯基黄酮类化合物合成8-C-异戊烯基黄酮类化合物的Claisen重排反应的关键步骤进行了探讨.所有合成的化合物经¹H NMR、¹³C NMR和MS等结构确证.
关键词: 8-异戊烯基槲皮素-3-甲醚, 8-异戊烯基槲皮素-3,7,3',4'-四甲醚, Artochamin C, 微波促进Claisen重排
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.
Key words: 8-prenylquercetin-3-methyl ether, 8-prenylquercetin-3,7,3',4'-tetramethyl ether, artochamin C, microwave promoted Claisen rearrangement


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