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Rhodium-catalyzed cycloadditions to construct nitrogen heterocycles and progress towards the synthesis of ionomycin

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dc.contributor.authorOberg, Kevin Martin, author
dc.contributor.authorRovis, Tomislav, advisor
dc.contributor.authorKennan, Alan J., committee member
dc.contributor.authorFerreira, Eric M., committee member
dc.contributor.authorNeilson, James R., committee member
dc.contributor.authorKanatous, Shane B., committee member
dc.date.accessioned2007-01-03T06:40:46Z
dc.date.available2007-01-03T06:40:46Z
dc.date.issued2014
dc.description.abstractThe ability to construct molecules in a rapid, atom-economical fashion is a major goal of organic chemistry. This work describes four topics; pyridone synthesis, mechanistic understanding in [2+2+2] cycloadditions, pyrimidinone synthesis, and progress towards ionomycin. The first chapter describes the synthesis of 4,6-substituted 2-pyridones and 3,5-substituted 4-pyridones from the rhodium-catalyzed [2+2+2] cycloaddition of two alkynes and an isocyanate. Our group demonstrated that an enantioselective rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and alkynes generates indolizidinone and quinolizidinone products. Although trends for product and regioselectivity were established, the underlying mechanism was unclear. The second chapter describes X-ray analysis of rhodium·phosphoramidite complexes in conjunction with other mechanistic work to elucidate a theory that explains product and regioselectivity in this reaction. This system is amazing in that it illuminates the factors contributing to oxidative cycloadditions in a spectacular fashion by delivering two different products. The third chapter describes the enantioselective synthesis of pyrimidinones from a rhodium-catalyzed [4+2] cycloaddition of α, β-unsaturated imines and isocyanates. The final chapter describes our group's progress toward the synthesis of ionomycin using rhodium-catalyzed desymmetrization of anhydrides with zinc nucleophiles.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierOberg_colostate_0053A_12242.pdf
dc.identifier.urihttp://hdl.handle.net/10217/82524
dc.languageEnglish
dc.language.isoeng
dc.publisherColorado State University. Libraries
dc.relation.ispartof2000-2019
dc.rightsCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.
dc.titleRhodium-catalyzed cycloadditions to construct nitrogen heterocycles and progress towards the synthesis of ionomycin
dc.typeText
dcterms.rights.dplaThis Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).
thesis.degree.disciplineChemistry
thesis.degree.grantorColorado State University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy (Ph.D.)

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