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Sensitized Photooxygenation of Cholesterol and Pseudocholesterol Derivatives via Singlet Oxygen
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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 5a-hydroperoxides.
Title: Sensitized Photooxygenation of Cholesterol and Pseudocholesterol Derivatives via Singlet Oxygen
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 5a-hydroperoxides.
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