C_(20)位含氧的对映-贝壳杉烷二萜A/B环系的构建  

Construction of the A/B ring system of C_(20)-oxygenated ent-kaurene diterpenoids

作　　者：谭伟 秦思循 曹瑞迪 刘小宇[1] 张丹[1] 秦勇[1] TAN Wei;QIN Sixun;CAO Ruidi;LIU Xiaoyu;ZHANG Dan;QIN Yong(West China School of Pharmacy,Sichuan University,Chengdu,Sichuan,610041 P.R.China)

机构地区：[1]四川大学华西药学院,四川成都610041

出　　处：《华西药学杂志》2021年第5期491-494,共4页West China Journal of Pharmaceutical Sciences

基　　金：国家自然科学基金资助项目(批准号:21971167)。

摘　　要：目的采用自由基环化策略,设计并构建了C_(20)位含氧的对映-贝壳杉烷二萜A/B环系的合成路线。方法以3-甲基-2-环己烯酮为原料,经Michael加成、氢氰化、Corey-Chaykovsky反应、自由基环化反应,得到目标A/B环系化合物。结果与结论该路线以4步、25.8%的总收率成功构建了A/B环,合成中的关键步骤为Ti^(3+)介导的自由基环化反应构建双环。OBJECTIVE To design and complete a synthetic route for construction of the A/B ring system of C_(20)-oxygenated ent-kaurene diterpenoids by radical cyclization.METHODS 3-Methyl-2-cyclohexen-1-one was employed as the starting material,which underwent a sequence of transformation including Michael addition,hydrocyanation,Corey-Chaykovsky reaction and radical cyclization to afford the target compound with A/B ring system.RESULTS and CONCLUSION This synthetic route allows assembly of the A/B unit in 4 steps with a total yield of 25.8%,in which a Ti^(3+)-mediated radical cyclization serves as the key step.

关 键 词：C_(20)-氧化态 对映-贝壳杉烷二萜 贝壳杉烷 MICHAEL加成 Corey-Chaykovsky反应 自由基环化 

分 类 号：R914[医药卫生—药物化学]