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dc.contributor.authorYvon, Brigitte L.en_US
dc.date.accessioned2007-05-18T20:03:11Z
dc.date.available2007-05-18T20:03:11Z
dc.date.issued2000-06-01T00:00:00Zen_US
dc.identifier.urihttp://hdl.handle.net/1993/1908
dc.description.abstractIn this thesis 'E,E'-dibenzylidenesuccinates were shown to exhibit atropisomerism, enantiomerism that originates from hindered rotation about the butadiene carbon - carbon single bond. In addition, the 'E,E'-dibenzylidenesuccinates were found to undergo photochemical electrocyclic reactions and thermal 1,5-sigmatropic hydrogen shifts to give 'cis'-1,2-dihydronaphthalenes. One of the photochemical electrocyclic reactions of the 'E,E'-dibenzylidenesuccinates was studied for its application to photodynamic therapy, a therapy in which a photoactive compound is used to photochemically produce a medically therapeutic benefit. Another one of these photocyclic reactions was explored as a general method for the synthesis of the trans'-1,2-dihydronaphthalene lignan, magnoshinin. Although the photochemical step in this reaction was ineffective, magnoshinin was successfully prepared by a more classical route. The possibility of substantially increasing the barrier to rotation about the carbon - carbon butadiene singlebond and/or prejudicing the formation of one atropisomer of an 'E,E'-dibenzylidenesuccinate by linking the two carboxyl groups with a rigid chiral auxiliary was investigated. (Abstract shortened by UMI.)en_US
dc.format.extent8524207 bytes
dc.format.extent184 bytes
dc.format.mimetypeapplication/pdf
dc.format.mimetypetext/plain
dc.language.isoengen_US
dc.rightsinfo:eu-repo/semantics/openAccess
dc.titleThe synthesis of lignans and lignan analogsen_US
dc.typeinfo:eu-repo/semantics/masterThesis
dc.typemaster thesisen_US
dc.degree.disciplinePlant Scienceen_US
dc.degree.levelMaster of Science (M.Sc.)en_US


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