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dc.contributor.authorShenje, Raynold
dc.date.accessioned2016-08-22T12:25:00Z
dc.date.available2016-08-22T12:25:00Z
dc.date.created2016-08
dc.date.issued2016-08-01
dc.date.submittedAugust 2016
dc.identifier.urihttp://hdl.handle.net/1853/55673
dc.description.abstractCyclopropanes 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).
dc.format.mimetypeapplication/pdf
dc.language.isoen_US
dc.publisherGeorgia Institute of Technology
dc.subjectRing-opening
dc.subjectStrained carbocyles
dc.subjectLewis acid catalysis
dc.subjectNatural products scaffolds
dc.titleStrained carbocycles as gateways to polycyclic molecular scaffolds and natural products targets
dc.typeDissertation
dc.description.degreePh.D.
dc.contributor.departmentChemistry and Biochemistry
thesis.degree.levelDoctoral
dc.contributor.committeeMemberMarder, Seth
dc.contributor.committeeMemberOyelere, Adegboyega
dc.contributor.committeeMemberCollard, David
dc.contributor.committeeMemberJones, Chirstopher
dc.contributor.committeeMemberFrance, Stefan
dc.date.updated2016-08-22T12:25:00Z


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