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    A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane.

    Access Status
    Fulltext not available
    Authors
    Bender, M.
    Schmidtmann, M.
    Summons, Roger
    Rullkötter, J.
    Christoffers, J.
    Date
    2015
    Type
    Journal Article
    
    Metadata
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    Citation
    Bender, M. and Schmidtmann, M. and Summons, R. and Rullkötter, J. and Christoffers, J. 2015. A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane.. Chemistry - A European Journal. 21 (35): pp. 12501-12508.
    Source Title
    Chemistry - A European Journal
    DOI
    10.1002/chem.201502148
    ISSN
    0947-6539
    URI
    http://hdl.handle.net/20.500.11937/39649
    Collection
    • Curtin Research Publications
    Abstract

    A diazonium ion derived from 18-aminoandrostane rearranged upon decomposition by a carbonium and a carbenium ion to furnish a mixture of a cyclopropanated compound and two D-homo-androstenes. Hydrogenation of this mixture gave the saturated hydrocarbons, 18-nor-D-homo-androstane and 5a,14ß-androstane, which are both fossil sterane biomarkers in Neoproterozoic crude oil. The so far unknown constitution and configuration as well as the geochemical genesis were established by this experiment. The starting material for this investigation, 18-aminoandrostane, was prepared in twelve steps from androstan-17-one (12.5% overall yield) with a Barton reaction as the key step.

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