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As part of our program on the synthesis and reactivity of the pyrrole-imidazole alkaloids from marine sponges, the synthesis of the 2-azido analog of the key marine natural product oroidin is reported. In addition, desaminooroidin and its alkyne analog were synthesized. Red-Al reduction of a 4-alkynylimidazole intermediate afforded the ( E )-alkene, without having to pass via the ( Z )-alkene. Coupling of 4,5-dibromopyrrole-2-carboxylic acid with 2-azidoimidazolylprop-2-en-1-amine was best achieved by EDCI-mediated coupling, which was superior to using the corresponding trichloromethylketone. Use of  t- BuOK in acetonitrile can be recommended for the coupling of non-azidated alkenyl and alkynylimidazoles. The azido analog of oroidin underwent click cycloadditions to imidazolyltriazoles.

Azido and desamino analogs of the marine natural product oroidin