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dc.contributor.advisorWilliams, Robert M.
dc.contributor.authorRafferty, Ryan J.
dc.contributor.committeememberShi, Yian
dc.contributor.committeememberCrans, Debbie C.
dc.contributor.committeememberPreito, Amy L.
dc.contributor.committeememberThamm, Douglas H.
dc.date.accessioned2007-01-03T05:58:42Z
dc.date.available2007-01-03T05:58:42Z
dc.date.issued2011
dc.description2011 Fall.
dc.descriptionIncludes bibliographical references.
dc.description.abstractHerein I discussed the total synthesis of hapalindoles J and U, the formal synthesis of hapalindole O, the proposed biosynthetic precursor to hapalindole K and efforts towards other hapalindole and ambiguine families of alkaloids. The hapalindoles and ambiguines both possess a highly functionalized 6:6:6:5, which I accessed over six synthetic steps via a developed silyl strategy with an overall 54% yield. Hapalindole J was synthesized in an overall 11% yield over eleven synthetic steps and hapalindole U in an overall 25% yield over thirteen synthetic steps from commercially available materials utilizing the silyl strategy developed. A formal synthesis of hapalindole O, intercepting Natsume's total synthesis, was accomplished as well via the developed silyl strategy. In addition, the synthesis of the proposed biosynthetic precursor to hapalindole K was accessed. Currently, this newly developed silyl strategy is being employed in accessing some of the more functionalized hapalindoles (such as K) as well as the complex ambiguine core.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierRafferty_colostate_0053A_10849.pdf
dc.identifierETDF2011500228CHEM
dc.identifier.urihttp://hdl.handle.net/10217/80352
dc.languageEnglish
dc.publisherColorado State University. Libraries
dc.relation.ispartof2000-2019 - CSU Theses and Dissertations
dc.rightsCopyright of the original work is retained by the author.
dc.subjectambiguine
dc.subjecttotal synthesis
dc.subjectsilyl
dc.subjecthapalindole
dc.titleTotal synthesis of hapalindoles J and J, formal synthesis of haplaindole O, synthesis of the proposed biosynthetic precursor to hapalindole K and work towards the ambiguine family of alkaloids
dc.typeText
dcterms.rights.dplaThe copyright and related rights status of this item has not been evaluated (https://rightsstatements.org/vocab/CNE/1.0/). Please refer to the organization that has made the Item available for more information.
thesis.degree.disciplineChemistry
thesis.degree.grantorColorado State University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy (Ph.D.)


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