Enantioselective Synthesis of ABCF Tetracyclic Framework of Daphniphyllum Alkaloid Calyciphylline N,Organic Letters

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Enantioselective Synthesis of ABCF Tetracyclic Framework of Daphniphyllum Alkaloid Calyciphylline N
Organic Letters ( IF 4.9 ) Pub Date : 2018-08-09 00:00:00 , DOI: 10.1021/acs.orglett.8b02202
Yunfei Li ₁ , Qiuyan Dong ₁ , Qinxia Xie ₁ , Pei Tang ₁ , Min Zhang ₁ , Yong Qin ₂

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Efforts toward the enantioselective synthesis of Daphniphyllum alkaloid calyciphylline N which leads to efficient preparation of the ABCF tetracyclic framework containing three bridgehead all-carbon quaternary stereocenters are described. This synthetic work features the utilization of an asymmetric conjugate addition to install the C5 all-carbon quaternary center, an efficient successive inter/intramolecular aldol sequence to build the critical bicyclo[2.2.2]octanone BC core, and a ring closing metathesis reaction followed by stereoselective Nagata conjugate cyanation to deliver the functionalized F ring.

中文翻译：

的ABCF四环框架的不对称合成虎皮楠生物碱Calyciphyllineñ

朝向的对映选择性合成的努力虎皮生物碱calyciphylline N的引线到含有三个ABCF四环框架的高效制备桥头全碳季立体有描述。这项合成工作的特点是利用不对称共轭加成物来安装C5全碳四元中心，有效的连续分子间/分子间羟醛序列，以构建关键的双环[2.2.2]辛烷酮BC核，然后进行闭环易位反应通过立体选择性长田共轭共轭氰化反应，以交付功能化的F环。

更新日期：2018-08-09

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