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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Detalles Bibliográficos
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
Descripción
Sumario: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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