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.
Org Lett. 2021 May 7;23(9):3264-3268. doi: 10.1021/acs.orglett.1c00720. Epub 2021 Apr 9.
The stereoselective total synthesis of siladenoserinols A and D has been accomplished using carbohydrate as a chiral template. The feature of this work is to build the medicinally privileged 6,8-DOBCO scaffold through a cascade reaction of hydrogenation/deacetalization/ketalization in a one-pot process, that is, to take advantage of a thermodynamically controlled bicyclization of polyhydroxyketone under HCl/MeOH reaction conditions. The current cost-effective synthetic strategy could facilitate the bioactivity investigation of siladenoserinols.
已使用碳水化合物作为手性模板完成了 siladenoserinols A 和 D 的立体选择性全合成。这项工作的特点是通过一锅法中的加氢/脱乙酰/缩酮化级联反应构建具有药物优势的 6,8-DOBCO 支架，即利用多羟基酮在 HCl/MeOH 反应条件下的热力学控制双环化反应。当前具有成本效益的合成策略可以促进 siladenoserinols 的生物活性研究。
