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    Synthetic studies on chaksine

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    EvansJ1970m-1b.pdf (25.17Mb)

    Date

    1970

    Author

    Evans, John Bruce

    Degree

    Master of Science

    Discipline

    Chemistry

    Subject

    Alkaloids Synthesis
    Chaksine

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    Abstract

    This thesis is concerned with the preliminary studies in the synthesis of a monoterpenoid alkaloid, chaksine. Diethyl methylmalonate was alkylated with 1,3-dibromo propane to give 2-(3-bromopropyl)-2-methylmalonate. Hydrolysis and decarboxylation of this product gave the mono acid which was then converted to the corresponding ethyl ester. Reduction with lithium borohydride yielded the primary alcohol to which a tetrahydropyran protective group was added. Alkylation with diethyl malonate followed by acylation with the mixed anhydride of isovaleric acid and carbobenzyloxyglycine gave diethyl (see document for formula).

    URI

    http://knowledgecommons.lakeheadu.ca/handle/2453/2203

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