Liu Xinlei, Li Shuyi, Wei Xinyu, Zhao Yu, Lai Daowan, Zhou Ligang, Wang Mingan
Department of Applied Chemistry, College of Sciences, China Agricultural University Beijing 100193 People's Republic of China
Department of Plant Pathology, College of Plant Protection, China Agricultural University Beijing 100193 People's Republic of China.
RSC Adv. 2020 Jan 8;10(3):1588-1594. doi: 10.1039/c9ra10316c. eCollection 2020 Jan 7.
The first total synthesis of Palmarumycin BG1-3, BG5-6, C and Guignardin E (1-7) were achieved by the same intermediate Palmarumycin C through a -benzyl cinchoninium chloride-catalyzed epoxidation, an organoselenium-mediated reduction, and a cerium(iii) chloride hydrate-promoted regioselective ring-opening and elimination of cyclic α,β-epoxy ketone as the key steps 6-7 step routes using 1,8-dihydroxynaphthalene (DHN) and 5-methoxytetralone as the starting materials in overall yields of 1.0-17.4%, respectively. Their structures and absolute configurations were characterized and determined by H, C NMR, IR, HR-ESI-MS and X-ray diffraction data. These compounds displayed significant inhibition activities against HCT116, U87-MG, HepG2, BGC823 and PC9 cell lines.
通过相同中间体棕榈霉素C，经氯化苄基辛可宁鎓催化环氧化、有机硒介导的还原以及水合氯化铈促进的区域选择性开环和环状α,β-环氧酮消除等关键步骤（6至7步路线），首次全合成了棕榈霉素BG1 - 3、BG5 - 6、C和吉纳尔丁E（1 - 7），分别以1,8 - 二羟基萘（DHN）和5 - 甲氧基四氢萘酮为起始原料，总收率分别为1.0% - 17.4%。通过氢谱、碳谱、红外光谱、高分辨电喷雾电离质谱和X射线衍射数据对它们的结构和绝对构型进行了表征和确定。这些化合物对HCT116、U87 - MG、HepG2、BGC823和PC9细胞系显示出显著的抑制活性。
