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    Strained carbocycles as gateways to polycyclic molecular scaffolds and natural products targets

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    SHENJE-DISSERTATION-2016.pdf (6.521Mb)
    Date
    2016-08-01
    Author
    Shenje, Raynold
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    Abstract
    Cyclopropanes and cyclobutanes, when activated with donor and acceptor groups, provide facile access to a plethora of interesting chemical scaffolds. Importantly, D-A cyclopropanes and cyclobutanes undergo efficient reactivity under mild Lewis acid conditions. This reactivity can be carried out in a modular fashion allowing for broad substrate scope enabling access to wider chemical space. In this thesis, D-A cyclopropanes and cyclobutanes were systematically used as chemical precursors to a variety of natural product-like scaffolds. Firstly, novel interrupted formal homo-Nazarov cyclizations were investigated and provided concise entry into α-arylated cyclohexenols, α-allylated cyclohexenols, and hexahydrobenzofurans. In a different pursuit, formal [5+2] cycloadditions, presumably occurring via D-A cyclobutane intermediates, afforded efficient, high-yielding and diastereoselective access to azepino[1,2-a]indoles and cyclohepta[b]indoles, two important backbones in the indole alkaloid family of natural products (Figure 6.1). Finally, homo-Nazarov-inspired cyclizations of strategically-chosen D-A cyclopropanes were successfully employed in the synthesis of hydropyrido[1,2-a]indoles (under continuous flow conditions) as well the dihydrodibenzo[b,d]furan core (featured in natural product propolisbenzofuran B).
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    http://hdl.handle.net/1853/55673
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    • Georgia Tech Theses and Dissertations [23877]
    • School of Chemistry and Biochemistry Theses and Dissertations [1525]

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