Geng Jialin, Ren Qidong, Chang Caizhu, Xie Xinni, Liu Jun, Du Yuguo
State Key Laboratory of Environmental Chemistry and Eco-Toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science Beijing 100085 China
School of Chemical Sciences, University of Chinese Academy of Sciences Beijing 100049 China.
RSC Adv. 2019 Apr 1;9(18):10253-10263. doi: 10.1039/c9ra01166h. eCollection 2019 Mar 28.
A divergent total synthesis of natural diacetylenic tetraols, petrosiol B and petrosiol D, was accomplished by taking advantage of a carbohydrate chiral template. In particular, petrosiol B, which is the first total synthesis so far, was achieved in 13 linear steps with a 10% overall yield applying Ohira-Bestmann homologation, NaH-mediated dehydrobromination, and Cu(i)-catalyzed Cadiot-Chodkiewicz coupling as the key reaction steps. The synthetic petrosiols B and D were subjected to the study on differentiation activities toward neuronal progenitor PC12 cells. Our results suggested that both petrosiol B and petrosiol D could induce the differentiation of neuronal progenitor PC12 cells the enhancement of Nrf2 activity. By comparing petrosiols B, D and their natural homologue E, petrosiol B displayed the most intensive cell differentiation activity and the highest Nrf2 activity enhancement as well.
利用碳水化合物手性模板完成了天然二乙炔四醇类化合物岩芹醇B和岩芹醇D的发散性全合成。特别值得一提的是，岩芹醇B的全合成是迄今为止的首次，以小原-贝斯特曼同系化反应、氢化钠介导的脱溴反应以及铜（I）催化的卡迪奥特-乔德凯维茨偶联反应作为关键反应步骤，经13步线性反应，总收率为10%。对合成得到的岩芹醇B和岩芹醇D进行了对神经祖细胞PC12细胞分化活性的研究。我们的结果表明，岩芹醇B和岩芹醇D均可诱导神经祖细胞PC12细胞分化，增强Nrf2活性。通过比较岩芹醇B、D及其天然同系物E，岩芹醇B表现出最强的细胞分化活性以及最高的Nrf2活性增强效果。
