摘要/Abstract

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¹H NMR、¹³C 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.
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
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 ¹H NMR and ¹³C NMR spectra while at the same time provided references for future isolation, identification, and discrimination of xanthochymol from its side chain structural isomers.
Key words: polycyclic polyprenylated acylphloroglucinols (PPAPs), bicyclo[3.3.1]nonanes, Dieckmann condensation, domino reaction


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