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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Main Author: Yvon, Brigitte L.
Language:en_US
Published: 2007
Online Access:http://hdl.handle.net/1993/1908
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spelling 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
collection NDLTD
language en_US
sources NDLTD
description 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
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