Diastereoselective Total Synthesis of (±)-Schindilactone A, Part 2: Construction of the Fully Functionalized CDEFGH Ring System
Diastereoselective Total Synthesis of (±)-Schindilactone A, Part 2: Construction of the Fully Functionalized CDEFGH Ring System
复制标题
DOI：
10.1002/asia.201200364
复制
发表时间：
2012-10-01
影响因子：
4.1
通讯作者：
Yang, Zhen
中科院分区：
文献类型：
--
作者：
Li, Yong;Chen, Zhi-Xing;Yang, Zhen
成功地合成了五味子内酯A（1）CEFGH环系的高度复杂的模型化合物（2）。为了实现这一目标，开发并应用了几种合成方法，包括闭环复分解（RCM）和硫脲催化的PausonKhand反应。此外，还开发了两种独立的方法来构建模型化合物2的GH环，其关键步骤包括硫脲催化的羰基化成环、甲基化和顺序的RCM/oxa-Michael加成反应。本文开发的化学方法使人们对五味子内酯A（1）及其同类化合物的合成有了更深入的了解。
The successful synthesis of the highly complex model compound (2) of the CEFGH ring system of schindilactone A (1) is described. Several synthetic methodologies were developed and applied to achieve this goal, including ring-closing metathesis (RCM) and Cothiourea-catalyzed PausonKhand reactions. Furthermore, two independent approaches were developed for the construction of the GH ring of model compound 2, the key steps of which included Pdthiourea-catalyzed carbonylative annulation, methylation, and sequential RCM/oxa-Michael-addition reactions. The chemistry developed herein has provided a greater understanding of the synthesis of schindilactone A (1) and its analogous compounds of the same family.