笼状倍半萜类化合物瑞香狼毒素A的仿生立体选择性全合成
Bioinspired Stereoselective Total Synthesis of the Caged Sesquiterpenoid Daphnepapytone A.
作者信息
Zhang Yan, Yu Pengfei, Chen Wei, Li Jia, Liu Kai, Xie Xingang, Li Huilin, She Xuegong
机构信息
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu, P. R. China.
State Key Laboratory of Green Pesticide, Guizhou University, Guiyang 550025, P. R. China.
出版信息
Org Lett. 2025 May 30;27(21):5480-5484. doi: 10.1021/acs.orglett.5c01509. Epub 2025 May 15.
The first total synthesis of the novel caged sesquiterpenoid daphnepapytone A is disclosed. Key reactions include a Pauson-Khand cycloaddition to provide oleodaphone, a bioinspired photoinduced [2 + 2] cycloaddition to forge the cyclobutane-containing caged skeleton, and a C-H oxidation and reduction protocol to generate daphnepapytone A. Finally, the 17-step synthetic sequence is shortened to 4 steps in protecting group-free and exclusively stereoselective fashion.
首次公开了新型笼状倍半萜类化合物瑞香番荔枝酮A的全合成。关键反应包括通过Pauson-Khand环加成反应得到油瑞香酮，通过仿生光诱导[2 + 2]环加成反应构建含环丁烷的笼状骨架，以及通过碳氢氧化和还原反应生成瑞香番荔枝酮A。最后，17步的合成序列以无保护基且完全立体选择性的方式缩短至4步。
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