The synthesis of lignans and lignan analogs
| 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.degree.discipline | Plant Science | en_US |
| dc.degree.level | Master of Science (M.Sc.) | en_US |
| 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.identifier.uri | http://hdl.handle.net/1993/1908 | |
| dc.language.iso | eng | en_US |
| dc.rights | open access | en_US |
| dc.title | The synthesis of lignans and lignan analogs | en_US |
| dc.type | master thesis | en_US |