Clark J Stephen, Baxter Carl A, Dossetter Alexander G, Poigny Stéphane, Castro José L, Whittingham William G
WestCHEM, Department of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow, G12 8QQ, United Kingdom.
J Org Chem. 2008 Feb 1;73(3):1040-55. doi: 10.1021/jo702111u. Epub 2008 Jan 3.
The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.
采用一种新颖的合成策略合成了植物源倍半萜天然产物新莲辛二酸的三环核心结构。关键的合成转化步骤包括通过依次进行金属卡宾C-H插入反应和叶立德形成反应构建关键的双环醚桥中间体，以及通过环氧化物与羧酸的酸催化分子内环开环反应来安装新莲辛二酸的内酯部分。
