一种通用的仿生杂环双烯 Alder 方法，用于构建 Xenovulene A、Sterhirsutins A 和 B 的核心骨架。
A General Biomimetic Hetero-Diels-Alder Approach to the Core Skeletons of Xenovulene A and the Sterhirsutins A and B.
机构信息
Institute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ) , Leibniz Universität Hannover , Schneiderberg 1 B , 30167 Hannover , Germany.
出版信息
Org Lett. 2019 Feb 15;21(4):998-1001. doi: 10.1021/acs.orglett.8b04003. Epub 2019 Jan 29.
A biomimetic, regio- and stereoselective approach to the 5,6,11-tricyclic core skeleton of xenovulene A, as well as sterhirsutins A and B, is described. The key steps are a biomimetic inverse-electron-demand hetero-Diels-Alder cycloaddition of α-humulene and a ribose-derived vinyl ketone, followed by acid-catalyzed rearrangement of the 1,3-dioxolane that neighbors the resultant cyclic enol ether.
描述了一种仿生、区域和立体选择性方法，用于构建 xenovulene A、sterhirsutins A 和 B 的 5,6,11-三环核心骨架。关键步骤是α-葎草烯和核糖衍生的乙烯酮的仿生逆电子需求杂 Diels-Alder 环加成反应，随后是紧邻所得环状烯醇醚的 1,3-二氧戊环在酸催化下的重排。
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