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N-Heterocyclic carbene catalysis: application to the total synthesis of cephalimysin A, and development of multicatalytic cascade reactions

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dc.contributor.authorLathrop, Stephen Paul, author
dc.contributor.authorRovis, Tomislav, advisor
dc.contributor.authorWood, John L., committee member
dc.contributor.authorCrans, Debbie Catharina, committee member
dc.contributor.authorShores, Matthew P., committee member
dc.contributor.authorKanatous, Shane B., 1968-, committee member
dc.date.accessioned2007-01-03T05:15:44Z
dc.date.available2007-01-03T05:15:44Z
dc.date.issued2011
dc.description.abstractApplication of the N-Heterocyclic carbene catalyzed Stetter reaction to the total synthesis of 9-epi-cephalimysin A has been realized. The approach centers on the use of an asymmetric catalytic Stetter reaction to access the spirocyclic core of cephalimysin A. Specifically it was found that a photoisomerization/Stetter protocol allows rapid access to an intermediate readily amenable for further functionalization. This intermediate was further elaborated to three stereoisomers of the naturally occurring cephalimysin A. During the investigation of cephalimysin A an interesting side product was observed that led to the development of several multicatalytic cascade reactions utilizing N-heterocyclic carbenes. Specifically the pairing of secondary-amine catalysts with N-heterocyclic carbenes allowed for the synthesis of densely functionalized cyclopentanones in a single step. Moreover, a synergistic relationship was observed between the two catalysts. This partnership allowed for the products to be achieved in higher selectivity than would have been possible if conducting the reactions in a stepwise fashion.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierLathrop_colostate_0053A_10331.pdf
dc.identifier.urihttp://hdl.handle.net/10217/47287
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.subjectcarbenes
dc.subjectStetter reaction
dc.subjectcephalimysin A
dc.subjectcascade reactions
dc.subjectbenzoin reaction
dc.titleN-Heterocyclic carbene catalysis: application to the total synthesis of cephalimysin A, and development of multicatalytic cascade reactions
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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