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Molecules 2001, 6(1), 52-60; doi:10.3390/60100052
Article

Sensitized Photooxygenation of Cholesterol and Pseudocholesterol Derivatives via Singlet Oxygen

1, 2,* , 1, 1 and 2
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.
Received: 30 September 1998 / Revised: 4 September 2000 / Accepted: 19 September 2000 / Published: 16 January 2001
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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.
Keywords: Cholesterol and pseudocholesterol derivatives; ene reaction of singlet oxygen; photochemical damage Cholesterol and pseudocholesterol derivatives; ene reaction of singlet oxygen; photochemical damage
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Shuping, W.; Zhiqin, J.; Heting, L.; Li, Y.; Daixun, Z. Sensitized Photooxygenation of Cholesterol and Pseudocholesterol Derivatives via Singlet Oxygen. Molecules 2001, 6, 52-60.

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