Photooxygenation of some potentially skin‐photosensitizing furocoumarins: Imperatorin, alloimperatorin and its methyl ether and acetate derivatives
- 12 September 1991
- journal article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1991 (9), 967-970
- https://doi.org/10.1002/jlac.1991199101166
Abstract
The photooxygenation of imperatorin (1a) afforded the corresponding allylic hydroperoxides 2a and 3a in very good yields. Similarly, the photooxygenation of alloimperatorin derivatives 1c, d gave the allylic hydroperoxides 2c, d and 3c, d in quantitative yields. On the other hand, on photooxygenation of alloimperatorin (1b) exclusively the dienone hydroperoxide 4b was obtained. When the reaction time was prolonged, the bis(hydroperoxide) 5b was also formed by successive photooxygenation of 4b.This publication has 9 references indexed in Scilit:
- Geminal selectivity of singlet oxygen ene reactions. The nonbonding large group effectJournal of the American Chemical Society, 1990
- Quinol epoxides from p ‐cresol and estrone by photooxygenation and titanium(IV)‐ or vanadium(V)‐catalyzed oxygen transferEuropean Journal of Inorganic Chemistry, 1988
- Photochemical Reactions of the Natural Furocoumarin, ImperatorinBulletin of the Chemical Society of Japan, 1987
- Biologically active principles of crude drugs. Anti-allergic principles in "Cnidii monnieri".CHEMICAL & PHARMACEUTICAL BULLETIN, 1985
- On the Involvement of Singlet Oxygen in the Biosynthesis of Oxygenation Products of the Furocoumarin ImperatorineZeitschrift für Naturforschung B, 1984
- RELATION BETWEEN SOME PHOTOBIOLOGICAL PROPERTIES OF FUROCOUMARINS AND THEIR EXTENT OF SINGLET OXYGEN PRODUCTIONPhotochemistry and Photobiology, 1981
- Preference for the syn ene additions of 1O2 to 1-methylcycloalkenes. Correlation with ground-state geometryJournal of the American Chemical Society, 1980
- Site specificity in the singlet oxygen-trisubstituted olefin reactionJournal of the American Chemical Society, 1979
- Preparation and Skin-Photosensitizing Activity of Substituted PsoralensJournal of Pharmaceutical Sciences, 1977