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dc.contributor.author Yvon, Brigitte L. en_US
dc.date.accessioned 2007-05-18T20:03:11Z
dc.date.available 2007-05-18T20:03:11Z
dc.date.issued 2000-06-01T00:00:00Z en_US
dc.identifier.uri http://hdl.handle.net/1993/1908
dc.description.abstract In 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.extent 8524207 bytes
dc.format.extent 184 bytes
dc.format.mimetype application/pdf
dc.format.mimetype text/plain
dc.language en en_US
dc.language.iso en_US
dc.title The synthesis of lignans and lignan analogs en_US
dc.degree.discipline Plant Science en_US
dc.degree.level Master of Science (M.Sc.) en_US


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