Synthesis of 24-Noroleanolic Acid Derivatives

Epoxidation of 2-cyano-2,3-seco-24-nor-4(23)-ene derivatives of oleanolic acid with m -chloroper­oxy­benzoic acid, followed by treatment of the resulting epoxides with boron trifluoride–diethyl ether complex, afforded new 24-noroleanane derivatives whose structure was determined using two-dimensiona...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2021-09, Vol.57 (9), p.1405-1411
Main Authors: Zakirova, L. M., Tretyakova, E. V., Baikova, I. P., Kazakova, O. B.
Format: Article
Language:English
Subjects:
Acids
Chemistry
Chemistry and Materials Science
Diethyl ether
Epoxidation
NMR
Nuclear magnetic resonance
Organic Chemistry
Oxidation
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Summary:Epoxidation of 2-cyano-2,3-seco-24-nor-4(23)-ene derivatives of oleanolic acid with m -chloroper­oxy­benzoic acid, followed by treatment of the resulting epoxides with boron trifluoride–diethyl ether complex, afforded new 24-noroleanane derivatives whose structure was determined using two-dimensional NMR correlation techniques ( 1 H– 1 H COSY, 1 H– 1 H NOESY, 1 H– 13 C HSQC, 1 H– 13 C HMBC). Depending on the conditions, the reaction of methyl 2-cyano-2,3-seco-24-norolean-4(23)-ene-28-oate with m -chloroperoxybenzoic acid may be regioselective with the formation of 4(23)-epoxy or 12-oxo derivative, as well as allylic oxidation product of the isopropenyl moiety.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428021090037