Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering , Shaanxi Normal University , 620 West Chang'an Avenue , Xi'an 710119 , China.
J Am Chem Soc. 2018 Apr 25;140(16):5653-5658. doi: 10.1021/jacs.8b03015. Epub 2018 Apr 12.
Herein, we report the first total syntheses of complex cephalotaxus diterpenoids cephanolide B and C from commercially available 5-bromo-2-methylanisole. Key to the success of this synthetic route is a palladium-catalyzed cascade cyclization reaction, which allowed us to efficiently forge the 6-5-6 cis-fused tricyclic ring systems found in the entire family of cephalotaxus diterpenoids. Additionally, site-selective late-stage sp C-H bond oxidation served as a key strategic element in the chemical synthesis of cephanolide C.
在此，我们报告了从商业可得的 5-溴-2-甲基苯甲醚首次全合成复杂的三尖杉二萜类化合物 cephanolide B 和 C。此合成路线的关键是钯催化的级联环化反应，使我们能够有效地构建整个三尖杉二萜类家族中发现的 6-5-6 顺式稠合的三环体系。此外，选择性晚期 sp^C-H 键氧化在 cephanolide C 的化学合成中是一个关键的战略要素。
