Synthesis of the acylphloroglucinols rhodomyrtone and rhodomyrtosone B |
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| Authors: | Marius Morkunas,Linda Dube,Friedrich Gö tz,Martin E. Maier |
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| Affiliation: | 1. Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany;2. Interfakultäres Institut für Mikrobiologie und Infektionsmedizin (IMIT), Mikrobielle Genetik, Universität Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany |
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| Abstract: | In a sequential three-component coupling syncarpic acid, 3-methylbutanal and an acylated phloroglucinol were combined to the hydroxy ketone 3. Acid catalysis converted 3 directly to the natural product rhodomyrtosone B (2). The other isomer, the antibiotic rhodomyrtone (1) was obtained from 3 in a sequence of acid-catalyzed cyclization, retro Friedel–Crafts reaction, and reacylation. In preliminary assays both compounds showed potent antibiotic activity. |
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| Keywords: | Acylphloroglucinols Natural products Antibiotics Knoevenagel condensation Retro Friedel&ndash Crafts acylation |
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