大叶藤黄醇的全合成研究  

Studies toward the Total Synthesis of Xanthochymol

作　　者：王学颖 盘伊琳 郑昌武[1] 徐宏喜[1] Wang Xueying;Phang Yee Lin;Zheng Changwu;Xu Hongxi(School of Pharmacy,Shanghai University of Traditional Chinese Medicine,Shanghai 201203)

机构地区：[1]上海中医药大学中药学院,上海201203

出　　处：《有机化学》2021年第11期4421-4427,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.81973438)资助项目.

摘　　要：多环多异戊烯基间苯三酚(PPAPs)类天然产物大叶藤黄醇(xanthochymol)具有良好的抗癌和抗菌活性,目前没有任何关于其全合成的研究报道.本研究以3,3-二甲基戊二酸为起始原料,通过一系列步骤制备线性链状底物,再应用串联Dieckmann缩合反应构建双环[3.3.1]壬烷-2,4,9-三酮核心骨架.此方法成功地以11步反应实现了消旋体大叶藤黄醇的全合成,以10%的总收率得到了目标产物.通过本研究得到大叶藤黄醇侧链的一对非对映异构体,在^(1)H NMR、^(13)C NMR谱图上明确了它们之间的区别,也对未来分离鉴定和区分其侧链结构异构体提供了参考数据.Xanthochymol,a polycyclic polyprenylated acylphloroglucinol(PPAP)natural compound,has demonstrated good anticancer and antimicrobial properties.However,no related studies on the synthesis of xanthochymol have been reported hitherto.In this study,3,3-dimethylglutaric acid was used as the starting material to synthesize a key linear precursor via several steps,followed by a domino Dieckmann condensation reaction to construct the bicyclo[3.3.1]nonane-2,4,9-trione core skeleton.With that,the total synthesis of(±)-xanthochymol in 11 steps with a total yield of 10%has been first accomplished.By obtaining the side chain diastereomers of xanthochymol through this study,we have clarified the difference between them on the ^(1)H NMR and ^(13)C NMR spectra while at the same time provided references for future isolation,identification,and discrimination of xanthochymol from its side chain structural isomers.

关 键 词：多环多异戊烯基间苯三酚(PPAPs) 双环[3.3.1]壬烷 Dieckmann缩合 串联反应 

分 类 号：TQ460.1[化学工程—制药化工]