Studies toward the imidazolyl-quinolone core of the bromotyrosine-derived alkaloid ceratinadin B

This is the authors' abstract. We don't add key points for this paper.

A de novo synthesis of the imidazolyl quinolone core of the marine sponge-derived alkaloid ceratinadin B was developed from 1,4-dimethoxybenzene. An acid mediated Friedel-Crafts reaction of a γ-aminobutyric acid derivative provided an aryl ketone which after bromination gave rise to the 2-aminoimidazole via a Hantzsch reaction. Nitration and subsequent reduction delivered the corresponding aniline from which the quinolone was constructed via a Gould-Jacobs reaction. This short and efficient sequence sets the stage for an assault on ceratinadin B.