ISSN:
0170-2041
Keywords:
Epoxidation
;
Furocoumarins
;
Imperatorin
;
Alloimperatorin
;
Prangenin
;
Dioxirane, dimethyl-
;
Oxygen transfer
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Epoxidation of imperatorin (1a) by dimethyldioxirane (DMD) affords the natural product prangenin (2a) in excellent yield. Similarly, alloimperatorin (1b) and its methyl and acetate derivatives 1b-d are epoxidized with DMD to give the corresponding epoxides 2b-d in quantitative yields. Furthermore, the reaction of the imperatorin allylic hydroperoxide 1e with DMD, and for comparison with m-chloroperbenzoic acid (CPBA), yields the diastereomeric epoxy hydroperoxides (R*,S*)- and (R*,R*)-2e in low but of opposite diastereoselectivity. Thus, for DMD the (R*,S*)/(R*,R*-2e ratio is 56:44 and for CPBA 40:60.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201123
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