A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues
A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues
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DOI：
10.1055/s-0037-1611652
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发表时间：
2019-03-01
期刊：
影响因子：
2
通讯作者：
Maulide, Nuno
中科院分区：
文献类型：
--
作者：
Bauer, Adriano;Nam, Jun-Hyun;Maulide, Nuno
介绍了以市售原料定量合成胡椒碱的方法。该合成依赖于原位生成的铜酸盐对环丁烯内酯的立体选择性亲核攻击。如此形成的芳基取代的环丁烯自发地经历同旋4-电环开环以形成作为单一非对映异构体的4-芳基异戊烯酸。高产率的合成可以很容易地调节芳基和酰胺部分，用于合成广泛的胡椒碱类似物。
A quantitative synthesis of piperine from commercially available starting material is presented. The synthesis relies on a stereoselective nucleophilic attack of an in situ generated cuprate onto a cyclobutene lactone. The so-formed aryl-substituted cyclobutene spontaneously undergoes a conrotatory 4-electrocyclic ring opening to form the 4-aryl pentadienoic acid as a single diastereoisomer. The high-yielding synthesis can be easily modulated on the aryl and on the amide moiety for the synthesis of a wide range of piperine analogues.