Total Syntheses of (-)-Conidiogenone B, (-)-Conidiogenone, and (-)-Conidiogenol.,Angewandte Chemie International Edition

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Total Syntheses of (-)-Conidiogenone B, (-)-Conidiogenone, and (-)-Conidiogenol.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-06-05 , DOI: 10.1002/anie.202007247
Bo Xu ₁ , Wen Xun ₁ , Shaobin Su ₁ , Hongbin Zhai _{1,

2,

3}

Affiliation

Cyclopianes are novel diterpenes featuring a highly strained 6/5/5/5 tetracyclic core embedded with 6–8 consecutive stereocenters. The concise total syntheses of (−)‐conidiogenone B, (−)‐conidiogenone, and (−)‐conidiogenol have been accomplished in 14–17 steps. The present work features a HAT‐mediated alkene–nitrile cyclization to access the cis‐biquinane, a Nicholas/Pauson–Khand reaction to construct the linear triquinane, and a Danheiser annulation to afford the congested angular triquinane skeleton.

中文翻译：

（-）-Conidiogenone B，（-）-Conidiogenone和（-）-Conidiogenol的总合成。

Cyclopianes是新颖的二萜，具有高度紧张的6/5/5/5四环核，嵌有6-8个连续的立体中心。（-）-conidiogenone B，（-）-conidiogenone和（-）-conidiogenol的简明全部合成过程已完成14-17个步骤。本工作的特点是通过HAT介导的烯烃-腈环化反应来获得顺式-二喹烷，通过Nicholas / Pauson-Khand反应来构建线性三喹烷，并通过Danheiser环合法获得了拥挤的角三喹烷骨架。

更新日期：2020-06-05

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