Tetrahedron, Oct 7, 2013, Vol.69(40), p.8559(5)
To link to full-text access for this article, visit this link: http://dx.doi.org/10.1016/j.tet.2013.07.091 Byline: Marius Morkunas, Linda Dube, Friedrich Gotz, Martin E. Maier 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. Author Affiliation: (a) Institut fur Organische Chemie, Universitat Tubingen, Auf der Morgenstelle 18, 72076 Tubingen, Germany (b) Interfakultares Institut fur Mikrobiologie und Infektionsmedizin (IMIT), Mikrobielle Genetik, Universitat Tubingen, Auf der Morgenstelle 28, 72076 Tubingen, Germany Article History: Received 11 July 2013; Revised 22 July 2013; Accepted 29 July 2013
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