Wallichanol类天然产物ABC环系合成研究
收稿日期: 2020-08-01
修回日期: 2020-09-17
网络出版日期: 2020-10-12
基金资助
国家自然科学基金(21562011); 国家自然科学基金(21861010); 贵州省科技基金([2015]2047); 贵州省科技基金([2020]1Y108); 贵州省科技基金([2018]5781); 贵州省研究生教育案例库建设(KCALK2017012); 贵州大学人才工程([2014]36)
Synthesis of the ABC Ring System of Wallichanol Natural Product
Received date: 2020-08-01
Revised date: 2020-09-17
Online published: 2020-10-12
Supported by
the National Natural Science Foundation of China(21562011); the National Natural Science Foundation of China(21861010); the Science and Technology Foundation of Guizhou Province([2015]2047); the Science and Technology Foundation of Guizhou Province([2020]1Y108); the Science and Technology Foundation of Guizhou Province([2018]5781); the Case Base Construction Project for Guizhou Graduate Education(KCALK2017012); the Guizhou University Talent Project([2014]36)
Wallichanol是一类具有独特桥环结构的二萜天然产物. 以2-甲基-1,3-环己二酮作为起始原料, 通过高立体选择性的Diels-Alder反应和金催化的炔烃碳环化反应构建Wallichanol的ABC三环核心骨架, 共七步路线, 总收率为42%. 该合成工作为Wallichanol类天然产物全合成奠定了研究基础.
关键词： Wallichanol; Diels-Alder反应; 碳环化反应; 全合成
杨刚 , 冯翔宇 , 韩丛丛 , 陈洋 , 何述钟 . Wallichanol类天然产物ABC环系合成研究[J]. 有机化学, 2021 , 41(2) : 726 -730 . DOI: 10.6023/cjoc202008001
A rapid construction of the ABC ring of wallichanol is described. The synthesis features an efficient Diels-Alder reaction for the bicyclo[2.2.2]octane synthesis and a gold-catalyzed alkyne carbometalation for the cyclobutane synthesis. The overall yield of this 7-stepped synthesis is 42%. This strategy can pave the road towards the total synthesis of wallichanol.
Key words： wallichanol; Diels-Alder reaction; carbometalation; total synthesis
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