天然产物3'-prenylgenistein的全合成  

Total synthesis of the natural product 3'-prenylgenistein

作　　者：赵艳敏[1] 李红俊 谢一民 李森[1] ZHAO YanMin;LI HongJun;XIE YiMin;LI Sen(College of Chemical and Biological Engineering,Yinchuan University of Energy,Yinchuan 750105;Ningxia Academy of Metrology and Quality Inspection,Yinchuan 750411,China)

机构地区：[1]银川能源学院化学与生物工程学院,银川750105 [2]宁夏计量质量检验检测研究院,银川750411

出　　处：《北京化工大学学报（自然科学版）》2023年第5期59-63,共5页Journal of Beijing University of Chemical Technology(Natural Science Edition)

基　　金：宁夏高等学校科学研究项目(NYG2022135);宁夏自然科学基金项目(2020AAC03275)。

摘　　要：3'-prenylgenistein是从大豆中分离出来的新型异戊烯基异黄酮,该化合物具有重要的生物防御活性。以廉价的4-羟基苯甲醛和2,4,6-三羟基苯乙酮为起始原料,通过异戊烯基化、羟基保护、羟醛缩合、环化以及黄烷酮到异黄酮的重排等步骤,首次以13.4%的总产率完成了天然产物3'-prenylgenistein的全合成。所有新化合物的结构都经过核磁共振(1H NMR)、红外光谱(IR)和质谱(MS)确认。3'-prenylgenistein is a novel isopentenyl isoflavone isolated from soybean.It has significant biodefense activity.Based on cheap 4-hydroxybenzaldehyde and 2,4,6-trihydroxyacetophenone as starting materials,the total synthesis of 3'-prenylgenistein has been completed for the first time.The synthesis involved isopentenylation,hydroxyl protection,aldol condensation,cyclization and rearrangement of flavanone to isoflavones,giving an overall yield of 13.4%.The structures of all new compounds were confirmed by nuclear magnetic resonance(1H NMR)spectroscopy,infrared spectroscopy(IR)and mass spectrometry(MS).

关 键 词：3'-prenylgenistein 异戊烯基异黄酮 全合成 

分 类 号：O625.1[理学—有机化学]