Oxidation of Methyl 2-Cyano-3,4-seco-4(23)-Ene-Ursolate by Ozone

Oxidation by ozone in CH₂Cl₂of methyl 2-cyano-3,4-seco-4(23)-ene-ursolate formed the three 2-cyano-3,4-seco-4-oxo derivatives 11-oxours-12-ene, 12-hydroxy-4,11-dioxours-12-ene, and 12-oxours-11S,13R-oxetane. The last was formed by oxidation of intermediate 12-oxoursolate. Ozonolysis of the ursolic a...

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Bibliographic Details
Published in:Chemistry of natural compounds 2014-12, Vol.50 (6), p.1037-1041
Main Authors: Khusnutdinova, E. F, Kazakova, O. B, Lobov, A. N, Kukovinets, O. S
Format: Article
Language:English
Subjects:
Air pollution
chemical derivatives
Chemical properties
Explosives
Hypoglycemic agents
Medicine
Nitriles
oleanolic acid
Organic Chemistry
oxidation
Oxidation-reduction reaction
ozone
ozonolysis
Pharmacy
Plant Sciences
Resveratrol
ursolic acid
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Summary:Oxidation by ozone in CH₂Cl₂of methyl 2-cyano-3,4-seco-4(23)-ene-ursolate formed the three 2-cyano-3,4-seco-4-oxo derivatives 11-oxours-12-ene, 12-hydroxy-4,11-dioxours-12-ene, and 12-oxours-11S,13R-oxetane. The last was formed by oxidation of intermediate 12-oxoursolate. Ozonolysis of the ursolic acid derivative with two unsaturated bonds in the C-4(23) and C-12(13) positions was non-selective, in contrast with that reported previously for an analogous oleanolic-acid derivative.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-014-1154-y