Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China.
Org Biomol Chem. 2018 Feb 7;16(6):957-962. doi: 10.1039/c7ob02769a.
The first total syntheses of five natural eremophilane-type sesquiterpenoids were achieved in 4-12 steps via a common synthetic intermediate. The syntheses feature a double Michael addition, Robinson annulation, α-enolization of an unsaturated ketone, and Pd-catalyzed Suzuki coupling reaction to install the side chain. This synthetic strategy could be easily extended to other eremophilane-type sesquiterpenoids with similar bicyclic skeletons.
通过一个共同的合成中间体，首次以 4-12 步实现了五种天然埃雷莫芬烷型倍半萜的全合成。该合成方法的特点是双迈克尔加成、Robinson 环化、不饱和酮的α-烯醇化以及 Pd 催化的Suzuki 偶联反应来安装侧链。该合成策略可以很容易地扩展到其他具有类似双环骨架的埃雷莫芬烷型倍半萜。
