Asymmetric Total Synthesis of Propindilactone G, Part 3: The Final Phase and Completion of the Synthesis
Asymmetric Total Synthesis of Propindilactone G, Part 3: The Final Phase and Completion of the Synthesis
复制标题
丙二内酯 G 的不对称全合成，第 3 部分：合成的最后阶段和完成
DOI：
10.1002/asia.201600131
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发表时间：
2016-05-06
影响因子：
4.1
通讯作者：
Yang, Zhen
中科院分区：
文献类型：
--
作者：
Liang, Xin-Ting;You, Lin;Yang, Zhen
Two independent synthetic approaches were evaluated for the final phase of the asymmetric total synthesis of propindilactone G (1). The key steps that led to the completion of the asymmetric total synthesis included: 1) an intermolecular oxidative heterocoupling reaction of enolsilanes to link the core structure to the side chain; 2) an intermolecular Wittig reaction for the formation of the alpha,beta,gamma,delta-unsaturated ester; and 3) a regio- and stereoselective OsO4-catalyzed dihydroxylation of an alpha,beta,gamma,delta-unsaturated enone, followed by an intramolecular lactonization reaction to afford the final product. These reactions enabled the synthesis of (+)-propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised. Furthermore, the direct oxidative coupling strategy for ligation of the core of propindilactone G with its side chain may find application in the syntheses of other natural products and complex molecules.
