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Construction of BCDEF Core of Andilesin C
Organic Letters ( IF 4.9 ) Pub Date : 2019-09-13 , DOI: 10.1021/acs.orglett.9b02791
Guili Zhu 1 , Chengying Zhou 1 , Song Chen 1 , Shaomin Fu 1 , Bo Liu 1, 2
Organic Letters ( IF 4.9 ) Pub Date : 2019-09-13 , DOI: 10.1021/acs.orglett.9b02791
Guili Zhu 1 , Chengying Zhou 1 , Song Chen 1 , Shaomin Fu 1 , Bo Liu 1, 2
Affiliation
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A synthetic study toward the BCDEF core skeleton of andilesin C is presented. Key elements involved iron-promoted intramolecular perezone-type [5 + 2] cycloaddition to install the BCD ring system simultaneously in a one-step, copper-catalyzed intramolecular cyclopropanation followed by BiCl3-promoted retro-aldol reaction to construct ring E and a one-pot manipulation involving reduction, lactonization, and isomerization to introduce the lactone ring F. We finally synthesized the congested BCDEF ring system of andilesin C, featuring four quaternary centers and two tertiary centers, by following a strategy with a 15-pot reaction and 11 purification operations.
中文翻译：
Andilesin C的BCDEF核心的构建
提出了对Andilesin C的BCDEF核心骨架的综合研究。关键元素涉及铁促进的分子内过环带型[5 + 2]环加成反应，以一步法，铜催化的分子内环丙烷化一步法同时安装BCD环系统，然后由BiCl 3促进的逆向醛醇缩合反应来构建环E和环氧基。一锅操作，涉及还原，内酯化和异构化，以引入内酯环F。我们最终通过遵循15锅反应的策略，合成了Andilesin C的拥挤BCDEF环系统，该系统具有四个四级中心和两个三级中心。 11个净化操作。
更新日期：2019-09-14
中文翻译：
Andilesin C的BCDEF核心的构建
提出了对Andilesin C的BCDEF核心骨架的综合研究。关键元素涉及铁促进的分子内过环带型[5 + 2]环加成反应，以一步法，铜催化的分子内环丙烷化一步法同时安装BCD环系统，然后由BiCl 3促进的逆向醛醇缩合反应来构建环E和环氧基。一锅操作，涉及还原，内酯化和异构化，以引入内酯环F。我们最终通过遵循15锅反应的策略，合成了Andilesin C的拥挤BCDEF环系统，该系统具有四个四级中心和两个三级中心。 11个净化操作。
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