Total syntheses of drimane-type sesquiterpenoids enabled by a gold-catalyzed tandem reaction.

Hang Shi, Lichao Fang, Ceheng Tan, Lili Shi, Weibin Zhang, Chuang-chuang Li, Tuoping Luo, Zhen Yang

Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, China.

Journal of the American Chemical Society 2011 Sep 28

filter terms:

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.

Citation

Hang Shi, Lichao Fang, Ceheng Tan, Lili Shi, Weibin Zhang, Chuang-chuang Li, Tuoping Luo, Zhen Yang. Total syntheses of drimane-type sesquiterpenoids enabled by a gold-catalyzed tandem reaction. Journal of the American Chemical Society. 2011 Sep 28;133(38):14944-7