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    Testing the boundaries of novel Friedel-Crafts-type methodologies inspired by n-heteroaromatic medicinal targets

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    LIGON-DISSERTATION-2019.pdf (25.70Mb)
    Date
    2019-03-29
    Author
    Ligon, Evelyn
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    Abstract
    Methodology development is an essential pursuit to enable the synthesis of pharmaceutically-relevant targets. The emergent concept of privileged scaffolds has provided a framework for focused synthetic methodology development toward polycyclic heteroaromatic compounds with inherent and important bioactivities. This thesis explores novel applications of the Friedel-Crafts reaction toward three medicinal compounds and their privileged scaffolds: flubromazepam, a 1,4-benzodiazepine; tronocarpine, a tetrahydro-7,11-methanoazocino[1,2-a]indole; and rhazinicine, a tetrahydroindolizine. Several 1,4-benzodiazepine positional isomers were synthesized and characterized for the first time. Additionally, significant advances in knowledge were accomplished toward the reactivity and stereochemical behavior of donor-acceptor bicyclo[3.1.0]hexanes, an understudied class of DACPs, in intramolecular ring-opening cyclizations, and a novel formal [3+2] cycloaddition of a C5-substituted D-A oxabicyclo[3.1.0]hexane was demonstrated.
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    http://hdl.handle.net/1853/61271
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    • School of Chemistry and Biochemistry Theses and Dissertations [1461]
    • Georgia Tech Theses and Dissertations [22398]

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