Approaches to the total synthesis of vernolepin

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dc.contributor.advisorHarding, K. E.
dc.creatorClement, Beverly Ann
dc.date.accessioned2020-08-21T21:09:33Z
dc.date.available2020-08-21T21:09:33Z
dc.date.issued1978
dc.descriptionVita.en
dc.description.abstractThe basic goal of this study was the development of an efficient approach to the total synthesis of vernolepin. Special attention was paid to the development of an efficient synthesis of bicycle[4.3.1]-dec-3-en-9,10-diones 9 and the synthesis of various 4-alkoxycrotonates. [Figure1] The reaction of the morpholine enamine of 4-cycloheptenone with 4-allyloxycrotonyl chloride produced dione 46. Dione 46 was readily converted to enone 72 by treatment with phenyltrimethylammonium tribromide followed by dehydrohalogenation utilizing N,N-dimethylformamide, lithium carbonate and lithium bromide. Enone 72 was converted to enone 73 by treatment with ethylene glycol, benzene and a trace of p-toluenesulfonic acid. Enone 73 was readily converted to adduct 76, which is a bisnorvernolepin synthon, by utilization of a divinyl cuprate. [Figure2]en
dc.format.digitalOriginreformatted digitalen
dc.format.extentxvi, 208 leavesen
dc.format.mediumelectronicen
dc.format.mimetypeapplication/pdf
dc.identifier.oclc5280897
dc.identifier.urihttps://hdl.handle.net/1969.1/DISSERTATIONS-235383
dc.language.isoeng
dc.publisher.digitalTexas A&M University. Libraries
dc.rightsThis thesis was part of a retrospective digitization project authorized by the Texas A&M University Libraries. Copyright remains vested with the author(s). It is the user's responsibility to secure permission from the copyright holder(s) for re-use of the work beyond the provision of Fair Use.en
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/
dc.subjectAntineoplastic agentsen
dc.subjectOrganic compoundsen
dc.subjectSynthesisen
dc.subjectMajor chemistryen
dc.subject.classification1978 Dissertation C626
dc.subject.lcshAntineoplastic agentsen
dc.subject.lcshOrganic compoundsen
dc.subject.lcshSynthesisen
dc.titleApproaches to the total synthesis of vernolepinen
dc.typeThesisen
dc.type.genredissertationsen
dc.type.materialtexten
thesis.degree.grantorTexas A&M Universityen
thesis.degree.nameDoctor of Philosophyen

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