Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, China.
J Am Chem Soc. 2011 Sep 28;133(38):14944-7. doi: 10.1021/ja206837j. Epub 2011 Sep 2.
Development of a gold-catalyzed tandem reaction of 1,7-diynes with both internal and external nucleophiles was realized, which constructed five chemical bonds, two rings, and two stereogenic centers in a single step. Based on the novel cascade transformation, we achieved a unified strategy toward the stereoselective total syntheses of C-15 oxygenated drimane-type sesquiterpenoids and their analogues, which provided the natural products kuehneromycin A, antrocin, anhydromarasmone, and marasmene as a proof-of-concept study.
发展了一种金催化的 1,7-二炔与内部和外部亲核试剂的串联反应,该反应在一步中构建了五个化学键、两个环和两个手性中心。基于这一新的级联转化,我们实现了 C-15 含氧二萜型倍半萜及其类似物的立体选择性全合成的统一策略,该策略为天然产物 kuehneromycin A、antrocin、anhydromarasmone 和 marasmene 的概念验证研究提供了支持。