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    Development of multicomponent assembly processes and their application to the synthesis of novel heterocyclic scaffolds and the total synthesis of actinophyllic acid : application of an iminium ion mediated cascade

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    GRANGER-DISSERTATION-2013.pdf (13.75Mb)
    Date
    2013-08
    Author
    Granger, Brett Adam
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    Abstract
    Several novel multicomponent assembly processes have been developed for the preparation of a diverse array of complex heterocyclic systems from relatively simple starting materials. These studies resulted in the discovery of a new quinazolone forming reaction, which was applied to the one-step synthesis of the quinazolinocarboline alkaloid rutaecarpine. Biological screening of these complex heterocycles culminated in the identification of a potent sigma-2 receptor ligand. A novel N-acyliminium ion mediated cascade reaction was employed for the concise synthesis of (±)-actinophyllic acid. The completion of the synthesis relied on the development of a reaction sequence that avoided a potentially detrimental fragmentation process. Furthermore, several anti-cancer compounds were identified through a diverted total synthesis approach.
    Department
    Chemistry
    Description
    text
    Subject
    Total synthesis
    Natural products
    Organic chemistry
    URI
    http://hdl.handle.net/2152/26089
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