尾-Selective C鈥揌 Arylation of Pyrroles Leading to Concise Syntheses of Lamellarins C and I

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• 作者：Kirika Ueda ; Kazuma Amaike ; Richard M. Maceiczyk ; Kenichiro Itami ; Junichiro Yamaguchi
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：September 24, 2014
• 年：2014
• 卷：136
• 期：38
• 页码：13226-13232
• 全文大小：524K
• ISSN：1520-5126

文摘

The first general 尾-selective C鈥揌 arylation of pyrroles has been developed by using a rhodium catalyst. This C鈥揌 arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of pyrrole-derived natural products and pharmaceuticals. As such, we have successfully synthesized polycyclic marine pyrrole alkaloids, lamellarins C and I, by using this 尾-selective arylation of pyrroles with aryl iodides (C鈥揌/C鈥揑 coupling) and a new double C鈥揌/C鈥揌 coupling as key steps.