Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid.
Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid.
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DOI：
10.1021/jacs.9b03751
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发表时间：
2019-03
影响因子：
15
通讯作者：
Aneta Turlik;Yifeng Chen;Anthony C Scruse;Timothy R. Newhouse
中科院分区：
文献类型：
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作者：
Aneta Turlik;Yifeng Chen;Anthony C Scruse;Timothy R. Newhouse
报道了重排贝壳杉烷型二萜化合物principinol D的全合成。该grayanane天然产物通过会聚片段偶联方法构建，其中中心七元环在后期合成。双环[3.2.1]辛烷片段通过Ni催化的α-乙烯基化反应获得。战略减少包括非对映选择性SmI 2介导的酮还原与PhSH和一个新的协议选择性酯还原酮的存在下。本文报道的收敛策略可能是更大类贝壳杉烷二萜类化合物的入口点。
The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central seven-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI2-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.