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Catalytically generated acyl triazoliums as versatile acylating reagents and progress toward the total synthesis of okilactomycin

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dc.contributor.authorWheeler, Philip Andrew Merris, author
dc.contributor.authorRovis, Tomislav, advisor
dc.contributor.authorShi, Yian, committee member
dc.contributor.authorFerreira, Eric, committee member
dc.contributor.authorShores, Matthew, committee member
dc.contributor.authorFisk, John D., committee member
dc.date.accessioned2007-01-03T04:54:55Z
dc.date.available2007-01-03T04:54:55Z
dc.date.issued2013
dc.description.abstractThe first chapter of this dissertation describes the development of reactions involving the NHC-catalyzed acylation of carbon and nitrogen nucleophiles. The overall goal of this work was to expand the scope of the NHC-redox reaction manifold and improve its applicability to the synthesis of products that would be useful to the organic chemistry community. An efficient and simple procedure for the preparation of amides from amine hydrochloride salts and α,β-unsaturated aldehydes was developed. This procedure was then applied to the asymmetric synthesis of α-fluoroamides which are valuable building blocks for the preparation of fluorinated compounds that are highly sought after in pharmaceutical, material, and agrichemical applications. The second chapter describes efforts toward the total synthesis of the complex polyketide natural product okilactomycin, enabled by the rhodium-catalyzed desymmetrization of 3,5-dimethylglutaric anhydride developed previously by our group. Progress includes construction of the entire carbon skeleton in two fragments, poised to be unified and elaborated to the natural product by closely precedented steps. This progress demonstrates the potential of the catalytic, enantioselective desymmetrization of anhydrides to build complexity in rapid fashion.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierWheeler_colostate_0053A_11611.pdf
dc.identifier.urihttp://hdl.handle.net/10217/78884
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.subjectNHC
dc.subjectpolyketide
dc.titleCatalytically generated acyl triazoliums as versatile acylating reagents and progress toward the total synthesis of okilactomycin
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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