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Studies towards the biomimetic synthesis of the stephacidin family of natural products and the concise and versatile synthesis of d,l-brevianamide B, C-12A-epi-malbrancheamide and structurally related analogs

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dc.contributor.authorValente, Meriah W. N., author
dc.contributor.authorWilliams, Robert M., advisor
dc.contributor.authorKurosu, Michio, committee member
dc.contributor.authorKennan, Alan J., committee member
dc.date.accessioned2022-11-28T17:46:43Z
dc.date.available2022-11-28T17:46:43Z
dc.date.issued2006
dc.description.abstractThe total synthesis of stephacidin A, avrainvillamide and stephacidin B was envisioned to proceed through a biomimetic intramolecular Diels-Alder cylcoaddition. The Diels-Alder precursor was thought to come from the coupling of (L)-prolinamide with a α-ketoacid indole, which would subsequently form the requisite azadiene. While the desired α-ketoacid indole was not stable enough to be synthetically formed, a pseudo- α-ketoacid was successfully designed. The coupling of this vinyl ether carboxylic acid indole moiety with (L)-prolinamide provides an interesting intramolecular Diels-Alder (IMDA) precursor, which might prove to be a useful synthetic prototype for the IMDA. A similar coupling between a pseudo-α-ketoacid and (L)-prolinamide was applied to a different system of compounds, which led to a biomimetically-inspired intramolecular Diels-Alder reaction that diastereoselectively formed the characteristic bicyclo[2.2.2]diazaoctane core of the brevianamides. A concise synthesis of d,l-brevianamide B was successfully designed through a Fischer indole reaction of the key tricyclic IMDA cycloadduct and phenyl hydrazine. This IMDA / Fischer indole route to form the indolic bicyclo[2.2.2]diazaoctane core has proven to be a versatile method to access C-12a-epi-malbrancheamide and structurally related analogs for biological activity studies.
dc.format.mediummasters theses
dc.identifier.urihttps://hdl.handle.net/10217/235848
dc.languageEnglish
dc.language.isoeng
dc.publisherColorado State University. Libraries
dc.relationCatalog record number (MMS ID): 991023653069703361
dc.relationQD421.V355 2006
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.subject.lcshIndole alkaloids -- Synthesis
dc.subject.lcshBiomimetics
dc.titleStudies towards the biomimetic synthesis of the stephacidin family of natural products and the concise and versatile synthesis of d,l-brevianamide B, C-12A-epi-malbrancheamide and structurally related analogs
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.levelMasters
thesis.degree.nameMaster of Science (M.S.)

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