Sensitized Photooxygenation of Cholesterol and Pseudo- cholesterol Derivatives via Singlet Oxygen

3-Substituted cholesterols and 7-substituted pseudocholesterols undergo a facile photooxygenation sensitized by 9, 10-dicyanoanthracene (DCA) and lumiflavin (LF) to give similar, oppositely-positioned enol derivatives. Both steroids showed the same reaction pattern associated with the endocyclic 5-...

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Autores principales: Shuping, Wu, Zhiqin, Jiang, Heting, Li, Li, Yang, Daixun, Zeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2001
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236460/
http://dx.doi.org/10.3390/60100052
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author Shuping, Wu
Zhiqin, Jiang
Heting, Li
Li, Yang
Daixun, Zeng
author_facet Shuping, Wu
Zhiqin, Jiang
Heting, Li
Li, Yang
Daixun, Zeng
author_sort Shuping, Wu
collection PubMed
description 3-Substituted cholesterols and 7-substituted pseudocholesterols undergo a facile photooxygenation sensitized by 9, 10-dicyanoanthracene (DCA) and lumiflavin (LF) to give similar, oppositely-positioned enol derivatives. Both steroids showed the same reaction pattern associated with the endocyclic 5- and 4-olefin units, respectively. The reaction was proposed to proceed via the ene reaction of singlet oxygen and subsequent rearrangement of the initially formed 5α-hydroperoxides.
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spelling pubmed-62364602018-11-20 Sensitized Photooxygenation of Cholesterol and Pseudo- cholesterol Derivatives via Singlet Oxygen Shuping, Wu Zhiqin, Jiang Heting, Li Li, Yang Daixun, Zeng Molecules Article 3-Substituted cholesterols and 7-substituted pseudocholesterols undergo a facile photooxygenation sensitized by 9, 10-dicyanoanthracene (DCA) and lumiflavin (LF) to give similar, oppositely-positioned enol derivatives. Both steroids showed the same reaction pattern associated with the endocyclic 5- and 4-olefin units, respectively. The reaction was proposed to proceed via the ene reaction of singlet oxygen and subsequent rearrangement of the initially formed 5α-hydroperoxides. MDPI 2001-01-16 /pmc/articles/PMC6236460/ http://dx.doi.org/10.3390/60100052 Text en © 2001 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Shuping, Wu
Zhiqin, Jiang
Heting, Li
Li, Yang
Daixun, Zeng
Sensitized Photooxygenation of Cholesterol and Pseudo- cholesterol Derivatives via Singlet Oxygen
title Sensitized Photooxygenation of Cholesterol and Pseudo- cholesterol Derivatives via Singlet Oxygen
title_full Sensitized Photooxygenation of Cholesterol and Pseudo- cholesterol Derivatives via Singlet Oxygen
title_fullStr Sensitized Photooxygenation of Cholesterol and Pseudo- cholesterol Derivatives via Singlet Oxygen
title_full_unstemmed Sensitized Photooxygenation of Cholesterol and Pseudo- cholesterol Derivatives via Singlet Oxygen
title_short Sensitized Photooxygenation of Cholesterol and Pseudo- cholesterol Derivatives via Singlet Oxygen
title_sort sensitized photooxygenation of cholesterol and pseudo- cholesterol derivatives via singlet oxygen
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236460/
http://dx.doi.org/10.3390/60100052
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AT hetingli sensitizedphotooxygenationofcholesterolandpseudocholesterolderivativesviasingletoxygen
AT liyang sensitizedphotooxygenationofcholesterolandpseudocholesterolderivativesviasingletoxygen
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