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  • 1
    Electronic Resource
    Electronic Resource
    Neuartige Umlagerungen in der Pregnanseitenkette (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 991-995 
    Details
    ISSN: 0170-2041
    Keywords: Steroids ; Pregnane, derivatives ; Androstane, derivatives ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: New Rearrangements in the Pregnane Side ChainReaction of 17-acetoxy-21-(acetylthio)-4-pregnene-3,20-dione (3) with a large excess of sodium azide in methanol yields a mixture of rearrangement products consisting of the methyl etianate 11 and the spirodithiolanone 12. The influence of temperature and solvent on the progress of the reaction has been studied. In order to obtain further informations pertaining to the mechanism of rearrangement, the compounds 4-10, the 6α-methyl and the D-homo substances 13b and 13d have been synthesized and subjected to the conditions of rearrangement.
    Notes: 17-Acetoxy-21-(acetylthio)-4-pregnen-3,20-dion (3) reagiert mit einem großen Überschuß an Natriumazid in Methanol zu einem Gemisch der Umlagerungsprodukte Etiansäure-methylester 11 und Spirodithiolanon 12. Der Reaktionsablauf wird in Abhängigkeit von Reaktionstemperatur und Lösungsmittel untersucht. Um weitere Einblicke in einen möglichen Umlagerungsmechanismus zu gewinnen, werden die Verbindungen 4-10, die 6α-Methyl- und die D-Homoverbindungen 13b und 13d als Modellsubstanzen synthetisiert und den Umlagerungsbedingungen unterworfen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890256
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  • 2
    Electronic Resource
    Electronic Resource
    Strukturanalyse von Steroid-17-spiro-dithiolanonen (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 1003-1006 
    Details
    ISSN: 0170-2041
    Keywords: Steroids ; Androstane, derivatives ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Structure Elucidation of Steroid-17-spiro-dithiolanonesThe structures of seven androstane-17-spiro-3′-(1′,2′-dithiolan)-4′-ones were elucidated with IR, CD, 1H NMR, and mass spectrometry and X-ray analysis. All compounds possess (17R) configuration (17β-CO, 17α-S). One corresponding D-homo compound has the same stereochemistry (17aR).
    Notes: Mit IR-, CD-, 1H-NMR- und Massen-Spektrometrie sowie Röntgenstrukturanalyse wurden die Strukturen von sieben Androstan-17-spiro-3′-(1′,2′-dithiolan)-4′-onen bestimmt. Alle Verbindungen besitzen (17R)-Konfiguration (17β-CO, 17α-S). Gleiche Stereochemie (17aR) kommt auch einer entsprechenden D-Homoverbindung zu.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890258
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