Synthesis of Naamidine A and Selective Access to N2-Acyl-2-aminoimidazole Analogues

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• 作者：Joseph B. Gibbons ; Justin M. Salvant ; Rachel M. Vaden ; Ki-Hyeok Kwon ; Bryan E. Welm ; Ryan E. Looper
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：October 16, 2015
• 年：2015
• 卷：80
• 期：20
• 页码：10076-10085
• 全文大小：555K
• ISSN：1520-6904

文摘

A short and scalable synthesis of naamidine A, a marine alkaloid with a selective ability to inhibit epidermal growth factor receptor (EGFR)-dependent cellular proliferation, has been achieved. A key achievement in this synthesis was the development of a regioselective hydroamination of a monoprotected propargylguanidine to deliver N³-protected cyclic ene-guanidines. This permits the extension of this methodology to prepare N²-acyl analogues in a fashion that obviates the troublesome acylation of the free 2-aminoimidazoles, which typically yields mixtures of N²- and N²,N²-diacylated products.