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  • 1
    Electronic Resource
    Electronic Resource
    Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranonen (1991)
    Springer
    Monatshefte für Chemie 122 (1991), S. 145-156 
    Details
    ISSN: 1434-4475
    Keywords: Isobenzofuranone ; Garlicin ; 1H-NMR spectroscopy ; X-ray analysis ; Determination of configuration
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary Oxidation of isobenzofuranone1 yielded in a diastereoselective reaction epoxide2. Acidolysis of2 resulted in a mixture oftrans-glycols6 a (88%) and7 a (4%), which were separated by crystallization. The relative configuration of6 a and7 a at the chiral centers 3 a, 5, 6, and 7 a was determined by1H-NMR-spectroscopy and X-ray analysis of O-acetylated and 7 a-methylated derivatives.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809359
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  • 2
    Electronic Resource
    Electronic Resource
    Synthese und Konfigurationszuordnung eines potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranons (1989)
    Springer
    Monatshefte für Chemie 120 (1989), S. 349-355 
    Details
    ISSN: 1434-4475
    Keywords: Isobenzofuranone ; Garlicin ; 1H-NMR-spectroscopy ; Determination of configuration
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary Isobenzofuranone3 was prepared by KMnO4-oxidation of2. 3 was reacted to give acetals4–10, which adopt the boat-conformation.3 and its acylated derivatives11–13 on the other hand prefer the chair-conformation. The relative configurations of3–13 at the chiral centres 3a, 5, 6, and 7a were determined by1H-NMR-spectroscopy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00811748
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  • 3
    Electronic Resource
    Electronic Resource
    Synthese von Cotarnin-Iodid (1989)
    Springer
    Monatshefte für Chemie 120 (1989), S. 765-769 
    Details
    ISSN: 1434-4475
    Keywords: Croweacinaldehyde ; Isoquinoline ; Cotarnin iodide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary Starting from 4-methoxy-1,3-benzodioxol-5-carbaldehyde (croweacin aldehyde,3) a six-step synthesis of cotarnin iodide (9, 67% total yield) is described.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809970
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  • 4
    Electronic Resource
    Electronic Resource
    Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones (1992)
    Springer
    Monatshefte für Chemie 123 (1992), S. 741-747 
    Details
    ISSN: 1434-4475
    Keywords: Garlicin ; Isobenzofuranone ; Lactones ; Diastereoselective synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 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.
    Notes: 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00812323
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis of 4,7-Dihydroxyperhydroisobenzofuran-1-one and Comparison with Zwergal's Structure of “garlicin” (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 383-386 
    Details
    ISSN: 0170-2041
    Keywords: Diels-Alder reaction ; Isobenzofuran derivate ; Garlicin ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Diels-Alder reaction of 2-(benzoyloxy)furan (2) with maleic anhydride leads to the adduct 3 which, on hydrogenation, affords the exo anhydride 4a (71%) and endo anhydride 4b (2.4%). The regioselective reduction of 4a and 4b with NaBH4 leads to the lactones 5a and 5b, respectively. Base-catalyzed cleavage of 5a gives the keto lactone 6 or dimethyl acetal 7, depending on the reaction conditions. Catalytic hydrogenation of keto lactone 6 results in the diastereoselective formation of the title compound 8a which has been converted into the acetate 8b and trifluoroacetate 8c. The structure and properties of the dihydroxylactone 8a are discussed in comparison with garlic compound “garlicin”.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199219920167
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    Paper (German National Licenses)
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