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The application of new methodology to complex molecule synthesis: studies toward the synthesis of pordamacrine A and liphagal

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dc.contributor.authorSeizert, Curtis A., author
dc.contributor.authorKennan, Alan, advisor
dc.contributor.authorFerreira, Eric, committee member
dc.contributor.authorChen, Eugene, committee member
dc.contributor.authorPrieto, Amy, committee member
dc.contributor.authorHansen, Jeffrey, committee member
dc.date.accessioned2015-08-27T03:56:51Z
dc.date.available2015-08-27T03:56:51Z
dc.date.issued2015
dc.description.abstractThe coevolution of organic synthesis and methodology has contributed greatly to the growth of both fields. This has been enabled by the invention of new methods during the prosecution of a synthesis in order to solve an unforeseen problem as well as by the novel application of independently developed methods to complex synthetic settings. Our own studies have encompassed both of these strategies, and we present their results herein. Our initial efforts consisted of synthetic studies towards the complex hexacyclic alkaloid pordamacrine A. This molecule presented many difficulties, and we were forced develop and employ new methods in its synthesis. Ultimately, these studies were stymied by the difficulty of forming the central carbocyclic ring system of this molecule. Among the methods used in the synthesis of pordamacrine A was a variant of a previously reported boron promoted Ireland-Claisen rearrangement. This rearrangement has been reported in very few papers in the literature, and many details of the reaction were undisclosed at the outset of ourstudies. We report here our investigations of the scope and stereochemical features of this rearrangement. Finally, methods based on the use of Pt carbenoids have formed a central element in our group's research focus. We apply here the use of this intermediate to the synthesis of liphagal, a complex tetracyclic compound. Our explorations of Pt-catalyzed cycloaddition reactions based on Pt carbenoids in this study have shed valuable light on the scope of this method. Though our studies culminated in a formal synthesis of an epimer of the natural product, we expect that future work towards liphagal will be able to use this methodology to make the correct diastereomer of liphagal, potentially in enantioenriched form.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierSeizert_colostate_0053A_12828.pdf
dc.identifier.urihttp://hdl.handle.net/10217/166875
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.subjectcatalysis
dc.subjectliphagal
dc.subjectsynthesis
dc.subjectIreland-Claisen
dc.subjectboron
dc.subjectplatinum
dc.titleThe application of new methodology to complex molecule synthesis: studies toward the synthesis of pordamacrine A and liphagal
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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