Nature of the transformations of oleanolic acid in an acid medium

descriptionPublicationkeyboard_double_arrow_right Article 01 Jan 1986 English Publisher:Springer Science and Business Media LLCJournal:Chemistry of Natural Compounds, volume 22, pages 295-297 (issn: 0009-3130, eissn: 1573-8388,

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Authors: A. A. Savina; D. A. Fesenko; V. I. Sheichenko; A. N. Shavlinskii;

doi: 10.1007/bf00598299

Nature of the transformations of oleanolic acid in an acid medium

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Abstract

3-Trifluoroacetoxyoleanolic acid and 3-trifluoroacetoxyolean-13(18)-en-28-oic acid have been isolated from the mixture of the products of the transformation of oleanolic acid in a trifluoroacetic acid medium, and their structures have been established with the aid of IR, PMR and mass spectra. The formation of these products indicates an unambiguous route of the stabilization of the intermediate carbocation with the charge on the C-13 atom. The hydroxy group at C-3 is esterified by the trifluoroacetic acid.

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