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Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones

Synthese enantiomerenreiner 5,6-Dihydroxy-isobenzofuranone und 5,6-Dihydroxy-4,7-methano-isobenzofuranone

  • Organische Chemie Und Biochemie
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Summary

Optically pure available lactones1 and5 were diastereoselectively oxidised tocis-diols2 and6 by KMnO4 and to epoxides3 and7 by 3-chloroperoxybenzoic acid. Epoxide3 was cleaved totrans-diol4, whereas hydrolysis of7 afforded tricyclic carboxylic acid8. Optic ally puredihydroxylactones2,4, and6 are valuable models for structure determination of the antimicrobial garlic component garlicin.

Zusammenfassung

Die in enatiomerenreiner Form verfügbaren Lactone1 und5 wurden durch diastereoselektive Oxidation mit KMnO4 zu dencis-Diolen2 und6 bzw. mit 3-Chlorperoxybenzoesäure zu den Epoxiden3 und7 umgesetzt. Das Epoxid3 liefert bei der Hydrolyse dastrans-Diol4, während aus7 die tricyclische Carbonsäure8 entsteht. Die optisch reinen Dihydroxylactone2,4 und6 können als Vergleichssubstanzen zur Strukturaufklärung des antimikrobiellen Knoblauchinhaltsstoffes Garlicin dienen.

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Universität Wien, A-1090, Wien, Austria

    Anna Edelsbacher, Ernst Urban & Waltraud Weidenauer

Authors
  1. Anna Edelsbacher
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  2. Ernst Urban
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  3. Waltraud Weidenauer
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Edelsbacher, A., Urban, E. & Weidenauer, W. Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones. Monatsh Chem 123, 741–747 (1992). https://doi.org/10.1007/BF00812323

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  • DOI: https://doi.org/10.1007/BF00812323

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