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

Sensitized Photooxygenation of Cholesterol and Pseudocholesterol Derivatives via Singlet Oxygen

1, 2,* email, 1, 1 and 2
Received: 30 September 1998; in revised form: 4 September 2000 / Accepted: 19 September 2000 / Published: 16 January 2001
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.
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
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MDPI and ACS Style

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.

AMA Style

Shuping W, Zhiqin J, Heting L, Li Y, Daixun Z. Sensitized Photooxygenation of Cholesterol and Pseudocholesterol Derivatives via Singlet Oxygen. Molecules. 2001; 6(1):52-60.

Chicago/Turabian Style

Shuping, Wu; Zhiqin, Jiang; Heting, Li; Li, Yang; Daixun, Zeng. 2001. "Sensitized Photooxygenation of Cholesterol and Pseudocholesterol Derivatives via Singlet Oxygen." Molecules 6, no. 1: 52-60.

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