Studies Toward the Imidazolyl-Quinolone Core of the Bromotyrosine-Derived Alkaloid Ceratinadin B

Authors

• Anasuya Ghorai, University of Texas at Arlington
• Xiaofeng Meng, University of Texas at Arlington
• Lesley A. Schmid, University of Texas at Arlington
• Evans Fosu, Mississippi State University
• Carl J. Lovely, Mississippi State University

MSU Affiliation

College of Arts and Sciences; Department of Chemistry

Creation Date

2026-10-02

Abstract

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.

Keywords

mycothiol S-amidase, Gould-Jacobs reaction, Hantzsch reaction, cross-coupling, electrophile-induced hydration

Publication Date

9-3-2026

Publication Title

Tetrahedron Letters

Publisher

Elsevier

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Rights

© 2026 The Authors

Recommended Citation

Ghorai, A., Meng, X., Schmid, L. A., Fosu, E., & Lovely, C. J. (2026). Studies toward the imidazolyl-quinolone core of the bromotyrosine-derived alkaloid ceratinadin B. Tetrahedron Letters, 185, 156245. https://doi.org/10.1016/j.tetlet.2026.156245