The synthesis of lignans and lignan analogs
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 electrocyc...
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ndltd-LACETR-oai-collectionscanada.gc.ca-MWU.1993-19082014-03-29T03:41:43Z The synthesis of lignans and lignan analogs Yvon, Brigitte L. 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.) 2007-05-18T20:03:11Z 2007-05-18T20:03:11Z 2000-06-01T00:00:00Z http://hdl.handle.net/1993/1908 en_US |
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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.) |
author |
Yvon, Brigitte L. |
spellingShingle |
Yvon, Brigitte L. The synthesis of lignans and lignan analogs |
author_facet |
Yvon, Brigitte L. |
author_sort |
Yvon, Brigitte L. |
title |
The synthesis of lignans and lignan analogs |
title_short |
The synthesis of lignans and lignan analogs |
title_full |
The synthesis of lignans and lignan analogs |
title_fullStr |
The synthesis of lignans and lignan analogs |
title_full_unstemmed |
The synthesis of lignans and lignan analogs |
title_sort |
synthesis of lignans and lignan analogs |
publishDate |
2007 |
url |
http://hdl.handle.net/1993/1908 |
work_keys_str_mv |
AT yvonbrigittel thesynthesisoflignansandlignananalogs AT yvonbrigittel synthesisoflignansandlignananalogs |
_version_ |
1716657569210040320 |