Sensitized Photooxygenation of Cholesterol and Pseudocholesterol Derivatives via Singlet OxygenReport as inadecuate


Sensitized Photooxygenation of Cholesterol and Pseudocholesterol Derivatives via Singlet Oxygen


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1

Research Laboratory of Photochemistry, Tongji University, Shanghai 200092, P. R. China

2

National Laboratory of Applied Organic Chemistry at Lanzhou University, Lanzhou 730000, P. R. China





*

Author to whom correspondence should be addressed.



Abstract 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. View Full-Text

Keywords: Cholesterol and pseudocholesterol derivatives; ene reaction of singlet oxygen; photochemical damage Cholesterol and pseudocholesterol derivatives; ene reaction of singlet oxygen; photochemical damage





Author: Wu Shuping 1, Jiang Zhiqin 2,* , Li Heting 1, Yang Li 1 and Zeng Daixun 2

Source: http://mdpi.com/



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