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    Part I: The total synthesis of (±)-securinine and (±)-allosecurinine and synthetic strategies for a second generation synthesis of the securinega alkaloids and Part II: The use of (+)-K252a in the semi-synthesis of indolocarbazole natural products and novel analogs thereof

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    http://hdl.handle.net/10217/82561
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    Abstract
    In part I, the total syntheses of (±)-securinine ((±)-1.001) and (±)-allosecurinine ((±)-1.003) are described. The syntheses feature the use of a Rh-initiated O—H insertion/Claisen rearrangement/1,2-allyl migration, which would allow for an enantioselective synthesis when an enantioenriched allylic alcohol (ie: (+)-1.137) is used. Three more steps generates the common intermediate imine 1.144, which upon reduction gives a pair of diastereomers. Protection of the free amine and a second reduction gives 1.146a and 1.146b, which were advanced to (±)-1.003 and (±)-1.001 respectively. Additional ...
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    Author(s)
    Levine, Samantha Roslyn

    Advisor(s)
    Ferreira, Eric M.

    Date Issued
    2014
    Format
    born digital; doctoral dissertations
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    • 2000-2019 - CSU Theses and Dissertations
    • Theses and Dissertations - Department of Chemistry

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