A novel synthesis of the 2-amino-1H-imidazol-4-carbaldehyde derivatives and its application to the efficient synthesis of 2-aminoimidazole alkaloids, oroidin, hymenidin, dispacamide, monobromodispacamide, and ageladine A

• Published in: Tetrahedron Vol. 66; no. 32; pp. 6224 - 6237
• Main Authors: Ando, Naoki, Terashima, Shiro
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 07.08.2010
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; NATURAL-PRODUCT; METABOLITES; ACID; ENANTIOSELECTIVE SYNTHESIS; ANALOGS; MATRIXMETALLOPROTEINASE INHIBITOR; (MMP)-12 INHIBITORY-ACTIVITY; SCEPTRIN; PYRROLE-IMIDAZOLE ALKALOIDS; MARINE SPONGE; Imidazole derivatives; Alkaloid; Amine; Imidazopyridine derivatives; Nitrogen heterocycle; Organic bromine compounds; Guanidines; Aldehyde; Chemical synthesis; Pyrrole derivatives
• ISSN: 0040-4020
• DOI: 10.1016/j.tet.2010.05.074

A novel synthesis of 2-amino-1H-imidazol-4-carbaldehyde derivatives was achieved by the reaction of tert-butoxycarbonylguanidine with 3-bromo-1,1-dimethoxypropan-2-one as a key step. The usefulness of the derivatives as building blocks was proved by accomplishing the efficient synthesis of the representative 2-aminoimidazole alkaloids, oroidin, hymenidin, dispacamide, monobromodispacamide, and ageladine A. (C) 2010 Elsevier Ltd. All rights reserved.