A Concise Total Synthesis of (-)-Mesembrine
A Concise Total Synthesis of (-)-Mesembrine
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(-)-松叶菊碱的简全合成
DOI：
10.1021/acs.joc.6b01908
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发表时间：
2016
影响因子：
3.6
通讯作者：
Yu Zhi-Xiang
中科院分区：
文献类型：
--
作者：
Wang Lu-Ning;Cui Qi;Yu Zhi-Xiang
从已知化合物出发，经过四步反应，以外消旋和不对称两种方式实现了美舒明的简明全合成。这里使用了两个关键反应。一种是Rh（I）催化的乙烯基环丙烷3c与CO的[5 + 1]环加成反应，另一种是Pd催化的β，γ-环己烯酮2c与芳基溴5的偶联反应（外消旋的dppe配体或不对称合成的（S）-Antphos配体）得到γ，γ-二取代α，β-环己烯酮1c。最后，Aza-Michael加成将1c转化为中间体。
A concise total synthesis of mesembrine (four steps from known compound) was achieved both racemically and asymmetrically. Two key reactions were used here. One is the Rh(I)-catalyzed [5 + 1] cycloaddition of vinylcyclopropane3cand CO. The other one is Buchwald’s Pd-catalyzed coupling reaction that coupled β,γ-cyclohexenone2cwith aryl bromide5(using dppe ligand for racemic or (S)-Antphos ligand for asymmetric synthesis) to give γ,γ-disubstituted α,β-cyclohexenone1c. Finally, aza-Michael addition converted1cto mesembrine.