环戊烷类化合物的非对映选择性合成：应用于瑞替加南酸A的ABCD四环核心结构的构建
Diastereoselective synthesis of cyclopentanoids: applications to the construction of the ABCD tetracyclic core of retigeranic acid A.
作者信息
Zhang Junlin, Wang Xiao, Li Shuang, Li Dian, Liu Song, Lan Yu, Gong Jianxian, Yang Zhen
机构信息
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055 (P. R. China).
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030 (P. R. China).
出版信息
Chemistry. 2015 Sep 1;21(36):12596-600. doi: 10.1002/chem.201502423. Epub 2015 Jul 16.
A concise and efficient approach for the construction of the tetracyclic carbon skeleton of retigeranic acid A is described. The key transformations include a novel Rh-catalyzed [3+2] cycloaddition of enyol to afford cyclopentanoid E, bearing two contiguous quaternary stereocenters at the bridgehead positions, and an intramolecular Pauson-Khand reaction to construct the advanced tetracyclic core structure of retigeranic acid A.
描述了一种构建瑞替加尼酸A四环碳骨架的简洁高效方法。关键转化包括烯醇的新型铑催化[3+2]环加成反应以得到在桥头位置带有两个相邻季碳立体中心的环戊烷类化合物E，以及分子内的鲍森-坎德反应以构建瑞替加尼酸A的高级四环核心结构。
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