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Progress towards the total synthesis of the welwitindolinone alkaloids and the discovery of a novel tandem O-H insertion Conia-ene cyclization

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dc.contributor.authorFreeman, David Blandy, author
dc.contributor.authorWood, John L., advisor
dc.contributor.authorKennan, Alan J., committee member
dc.contributor.authorFerreira, Eric M., committee member
dc.contributor.authorShores, Matthew P., committee member
dc.contributor.authorMcNeil, Michael R., committee member
dc.date.accessioned2007-01-03T05:15:55Z
dc.date.available2007-01-03T05:15:55Z
dc.date.issued2011
dc.description.abstractThe broth of blue-green algae Hapalosiphon wewitschii and Westiella intricate was shown to possess interesting biological activity, including insecticidal and P-glycoprotein inhibiting capabilities. Upon further investigation, the welwitindolinone alkaloids were isolated from the lipophilic extracts and shown to be responsible for the observed biological activity. Herein are described efforts towards the total synthesis of the welwitindolinone alkaloids and novel chemistry developed in the process. In efforts towards N-methylwelwitindolinone C isothiocyanate, we employed a sequential O-H insertion Claisen rearrangement to provide compounds capable of undergoing a [3+2] dipolar cycloaddition to access the bicyclo[4.3.1] core. Attempts to install the requisite quaternary center of N-methylwelwitindolinone C isothiocyanate during the [3+2] dipolar cycloaddition event were unsuccessful. Ultimately, a chloronium-ion semi-Pinacol rearrangement was utilized to install the key quaternary center. Due to complications encountered during the synthesis of N-methylwelwitindolinone C isothiocyanate we shifted our focus to N-methylwelwitindolinone D isonitrile. Investigation into the construction of the bridged ether embedded within N-methylwelwitindolinone D isonitrile led to the discovery of a novel tandem O-H insertion Conia-ene cyclization.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierFreeman_colostate_0053A_10293.pdf
dc.identifier.urihttp://hdl.handle.net/10217/47385
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.subjectalkaloids
dc.subjectwelwitindolinone
dc.subjectO-H insertion
dc.subjectConia-ene cyclization
dc.titleProgress towards the total synthesis of the welwitindolinone alkaloids and the discovery of a novel tandem O-H insertion Conia-ene cyclization
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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