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Synthesis of Rhodomyrtone Analogs Modified at C7 |
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| Authors: | Marvin Wenninger Prof. Dr. Martin E. Maier Dr. Aparna Viswanathan Ammanath Dr. Li Huang Prof. Dr. Friedrich Götz |
| Affiliation: | 1. Eberhard Karls Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany;2. Eberhard Karls Universität Tübingen, Mikrobielle Genetik, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin Tübingen (IMIT), Auf der Morgenstelle 28, 72076 Tübingen, Germany;3. Eberhard Karls Universität Tübingen, Mikrobielle Genetik, Interfakultäres Institut für Mikrobiologie und Infektionsmedizin Tübingen (IMIT), Auf der Morgenstelle 28, 72076 Tübingen, Germany Current address: Southwest Minzu University, Department of Preventive Veterinary Medicine, South Section, 1st Ring Road, Chengdu, 610041 Sichuan, China |
| Abstract: | We developed a route to rhodomyrtone analogs that feature different acyl groups at C7. Since electrophilic substitution reactions on the aryl part of the rhodomyrtone core led to C5 derivatives, the C5 position was blocked by a chlorine. Subsequent Duff type formylation followed by Grignard addition to the aldehyde group and oxidation gave various phenones. The benzyl protecting groups were removed by hydrogenation or boron tribromide. Some derivatives turned out to be quite active against multiple resistant Staphylococcus aureus strains and a rhodomyrtone resistant mutant (RomR). The chlorine at C5 seems to have a beneficial effect on the antibacterial activity. |
| Keywords: | acylphloroglucinol synthetic methods natural products rhodomyrtone structure-activity relationships |