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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 (CC BY 3.0).

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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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