Dokument: Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B
| Titel: | Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B | |||||||
| URL für Lesezeichen: | https://docserv.uni-duesseldorf.de/servlets/DocumentServlet?id=73005 | |||||||
| URN (NBN): | urn:nbn:de:hbz:061-20260421-135719-6 | |||||||
| Kollektion: | Publikationen | |||||||
| Sprache: | Englisch | |||||||
| Dokumententyp: | Wissenschaftliche Texte » Artikel, Aufsatz | |||||||
| Medientyp: | Text | |||||||
| Autoren: | Weber, Horst [Autor] Tran-Cong, Kim-Thao [Autor] Mayer, Bernhard [Autor] Reiss, Guido J. [Autor] Konovalova, Iryna S. [Autor] Passreiter, Claus M. [Autor] Appelhans, Marc S [Autor] Wood, Kenneth R [Autor] | |||||||
| Dateien: |
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| Stichwörter: | Melicope barbigera , new natural compounds , new heterocyclic ring systems , Melifoliones A and B , phenol oxidation , para-quinols | |||||||
| Beschreibung: | In addition to new acetophenones and 2H-chromenes, the dichlormethane extract from leaves of Melicope barbigera A. Gray (Rutaceae) afforded a mixture of the isomeric melifoliones A (1) and B (2) as well as an oxidation product of 2, whose structure was elucidated as the para-quinol 4. For an independent synthesis of 4 and its possible isomer 3, the required compounds 1 and 2 were synthesized as a mixture of the isomers starting from chromene 5, briefly heated in a closed microwave apparatus with catalytic amounts of acetic acid. Forced heating of 5 in acetic acid or use of stronger acids lead to the benzoxocin derivatives 6 and 7. Oxidation of melifoliones 1 and 2 under a great variety of oxidants and conditions failed to give 3 and 4. Iodine-containing oxidants yielded the products 8, 9, and 10. Combined oxidation with hydrogen peroxide and ferricyanide in alkaline solution resulted in an unexpected contraction of the acetyl phenol to a furanone ring, forming the derivatives 11 and 12, whose structures were confirmed by X-ray analysis. A hypothetical mechanism for the oxidative ring contraction is proposed. 11 and 12 are the first representatives of new heterocyclic ring systems that have not previously been described in the literature. | |||||||
| Rechtliche Vermerke: | Originalveröffentlichung: Weber, H., Tran-Cong, K.-T., Mayer, B., Reiss, G. J., Konovalova, I. S.,
Appelhans, M. S., Wood, K. R., & Paßreiter, C. (2026). Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B. Beilstein journal of organic chemistry, 22, 535–546. https://doi.org/10.3762/bjoc.22.39 [https://doi.org/10.3762/bjoc.22.39] | |||||||
| Lizenz: |  Dieses Werk ist lizenziert unter einer Creative Commons Namensnennung 4.0 International Lizenz | |||||||
| Fachbereich / Einrichtung: | Mathematisch- Naturwissenschaftliche Fakultät | |||||||
| Dokument erstellt am: | 21.04.2026 | |||||||
| Dateien geändert am: | 21.04.2026 |
