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Natural product chemistry, Part 132: Synthesis and oxidative cyclisation of 1,3-dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10H)-acridinone (glycocitrine-II)

Naturstoffchemie, 132. Mitt.: Synthese und oxidative Cyclisierung von 1,3-Dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10H)-acridinon (Glycocitrin-II)

  • Organische Chemie Und Biochemie
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Summary

Reaction of 1,3-dihydroxy-10-methyl-9(10H)-acridinone (1) and 1-bromo-3-methylbut-2-ene (mol. ratio 1:1) in tetrahydrofuran at 20°C in the presence of alumina gave prenylacidinones2 (glycocitrine-II) and8 and the diprenylacridinone9; with an excess of 1-bromo-3-methylbut-2-ene, the prenyldihydropyranoacridinones12 and13 were formed. Oxidation of glycocitrine-II (2) withm-chloroperbenzoic acid furnished the furanoacridinone5 and the pyranoacridinone6; dehydration of the latter compound gave noracronycine (10).

Zusammenfassung

1,3-Dihydroxy-10-methyl-9(10H)-acridinon (1) reagierte mit 1-Brom-3-methylbut-2-en (Mol.-Verhältnis 1:1) in Tetrahydrofuran bei 20°C in Gegenwart von Aluminiumoxid zu den Prenylacridinonen2 (Glycocitrin-II) und8 sowie dem Diprenylacridinon9. Bei Überschuß von 1-Brom-3-methylbut-2-en entstanden die Prenyldihydropyranoacridinone12 und13. Die Oxidation von Glycocitrin-II (2) mitm-Perchlorbenzoesäure liefert das Furanoacridinon5 und das Pyranoacridinon6. Die Dehydrierung von letzterem ergab Noracronycin (10).

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Authors and Affiliations

  1. Department of Applied Physical Sciences, The University of Ulster, Coleraine, Northern Ireland

    Michael F. Grundon & Wiltrud Probst

  2. Institut für Pharmazeutische Chemie, Westfälische Wilhelms-Universität Münster, D-4400, Münster, Federal Republic of Germany

    Johannes Reisch

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  1. Michael F. Grundon
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  2. Wiltrud Probst
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  3. Johannes Reisch
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Grundon, M.F., Probst, W. & Reisch, J. Natural product chemistry, Part 132: Synthesis and oxidative cyclisation of 1,3-dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10H)-acridinone (glycocitrine-II). Monatsh Chem 121, 157–163 (1990). https://doi.org/10.1007/BF00809528

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  • DOI: https://doi.org/10.1007/BF00809528

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