Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B

被引：122
|
作者：
Kieffer, Madeleine E. [1 ]
Chuang, Kangway V. [1 ]
Reisman, Sarah E. [1 ]
机构：
[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Div Chem & Chem Engn, Pasadena, CA 91125 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 15期
基金：
美国国家科学基金会;
关键词：
CONCISE TOTAL-SYNTHESIS; ONE-POT SYNTHESIS; ENANTIOSELECTIVE CONSTRUCTION; CYCLOTRYPTAMINE ALKALOIDS; PALLADIUM; PYRROLOINDOLINES; INDOLES; ALLYLATION; HODGKINSINE; TRYPTAMINES;
D O I：
10.1021/ja4023557
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.
引用
收藏
页码：5557 / 5560
页数：4
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