Convergent Synthesis of Kibdelone C
Convergent Synthesis of Kibdelone C
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Kibdelone C 的收敛合成
DOI：
10.1021/acs.orglett.8b00901
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发表时间：
2018-05-18
期刊：
影响因子：
5.2
通讯作者：
Gao, Shuanhu
中科院分区：
文献类型：
--
作者：
Dai, Yihua;Ma, Feixia;Gao, Shuanhu
从一株土壤放线菌中分离得到一种多环的天然口山酮基布地隆C。采用6 π电环化法构建了高度取代的二氢菲醇片段（B-C-D环）。InBr 3促进的内酯化反应被用来构建异香豆素环，该环作为形成异喹啉酮环（A-B环）的共同前体。一个关键的DMAP介导的oxa-Michael/aldol级联反应被开发来安装四羟基蒽酮片段（E-F环）。该方法为制备其衍生物和结构相关的天然产物提供了新的解决方案。
The synthesis of kibdelone C, a polycyclic natural xanthone isolated from a soil actinomycete, was achieved through a convergent approach. A 6 pi-electrocyclization was applied to construct the highly substituted dihydrophenanthrenol fragment (B-C-D ring). InBr3-promoted lactonization was employed to build the isocoumarin ring, which served as a common precursor for the formation of isoquinolinone ring (A-B ring). A key DMAP-mediated oxa-Michael/aldol cascade reaction was developed to install the tetrahydroxanthone fragment (E-F ring). This approach provides a new solution to prepare its derivatives and structurally related natural products.