Work

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

Year: 2015

Type: article

Abstract: 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 N(3)-protected cyclic ene-guanidines. This permits the extension of this methodology to prepare N(2)-acyl analogues in a fashion that obviates the troublesome acylation of the free 2-aminoimidazoles, which typically yields mixtures of N(2)- and N(2),N(2)-diacylated products.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5b01703

Authors: Joseph B. Gibbons, Justin M. Salvant, Rachel M. Vaden, Ki-Hyeok Kwon, Bryan E. Welm, Ryan E. Looper

Institutions: University of Utah, Oklahoma Medical Research Foundation

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green