Studies on bredinin. III. Chemical synthesis of bredinin. (A novel imidazole nucleoside).

Bredinin, a novel imidazole nucleoside, produced by Eupenicillium brefeldianum M-2166 was synthesized by the condensation of the trimethylsilyl derivative of 4 (5)-carbamoyl imidazolium-5 (4)-olate with 1, 2, 3, 5-tetra-O-acyl-β-D-ribofuranose in the presence of Friedel-Crafts catalysts (SnCl4, TiCl4) followed by deacylation. It was identical with natural bredinin. The absolute configuration was established as 4-carbamoyl-1-β-D-ribofuranosyl imidazolium-5-olate.