Sensitized photooxygenation of cholesterol and pseudocholesterol derivatives via singlet oxygen

Authors
Wu, SP Jiang, ZQ Li, HT Yang, L Zeng, DX
Citation
Sp. Wu et al., Sensitized photooxygenation of cholesterol and pseudocholesterol derivatives via singlet oxygen, MOLECULES, 6(1), 2001, pp. 52-60
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
MOLECULES
ISSN journal
14203049 → ACNP
Volume
6
Issue
1
Year of publication
2001
Pages
52 - 60
Database
ISI
SICI code
1420-3049(200101)6:1<52:SPOCAP>2.0.ZU;2-I
Abstract
3-Substituted cholesterols and 7-substituted pseudocholesterols undergo a f acile photooxygenation sensitized by 9, 10-dicyanoanthracene (DCA) and lumi flavin (LF) to give similar, oppositely-positioned enol derivatives. Both s teroids 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 init ially formed 5 alpha -hydroperoxides.