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  • 1
    Electronic Resource
    Electronic Resource
    Chemie und Stereochemie der Iridoide, XIV. Aucubin und Scandosid aus Catalpol (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 715-717 
    Details
    ISSN: 0170-2041
    Keywords: Aucubin ; Scandoside ; Catalpol ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chemistry and Stereochemistry of Iridoids, XIV.  -  Aucubin and Scandoside from CatalpolAucubin (9), scandoside (10), and its methyl ester [“feretoside” (11)] were obtained, in good yields, from catalpol (1). The absolute configurations of 9-11 were established by correlation to catalpol, whose X-ray crystal structure has previously been determined.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001137
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  • 2
    Electronic Resource
    Electronic Resource
    Chemie und Stereochemie der Iridoide, XVIII. Enantiomerenreines (+)-Cyclosarkomycin aus Catalpol (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 1213-1216 
    Details
    ISSN: 0170-2041
    Keywords: (+)-Cyclosarkomycin ; Catalpol ; Iridoids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chemistry and Stereochemistry of Iridoids, XVIII.  -  Enantiomerically Pure (+)-Cyclosarkomycin from CatalpolThe reaction of hexaacetylcatalpol (2) with peroxyformic acid results in hexaacetyl-3-formyloxy-4-hydroxycatalpol (3), which is cleaved to 4 and sorbit (4a) by reduction with LiAlH4. The mixture of 4/4a was acetylated and the resulting acetates 5/5a separated by column chromatography. The following reactions from 5 to 9 (reactions e - i of Scheme 1) are each nearly quantitative. Therefore, the isolation of the intermediates 6-8 was not necessary. The constitutions of 6-8 were proven by 13C-NMR spectroscopy. The (1S,2RS,5R)-2-hydroxy-3-oxabicyclo[3.3.0]octan-6-one (9) was purified by column chromatography and its oxidation by pyridinium chlorochromate (PCC) in dichloromethane leads to crystalline (+)-cyclosarkomycin (10) [yield 85%, based on 5].
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201202
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    Paper (German National Licenses)
    Fulltext
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