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Issue 28, 2014
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An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester): analogues, biological activities, and comparison with oleanolic acid derivatives

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Abstract

An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester) from commercially available ursolic acid, which features an oxidative ozonolysis-mediated C-ring enone formation, and provides the first access to ursolic acid-derived cyano enone analogues with C-ring activation. These new ursolic acid analogues show potent biological activities, with potency of approximately five-fold less than the corresponding oleanolic acid derivatives.

Graphical abstract: An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester): analogues, biological activities, and comparison with oleanolic acid derivatives

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Publication details

The article was received on 31 Mar 2014, accepted on 30 May 2014 and first published on 03 Jun 2014


Article type: Paper
DOI: 10.1039/C4OB00679H
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 5192-5200
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    An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester): analogues, biological activities, and comparison with oleanolic acid derivatives

    L. Fu, Q. Lin, K. T. Liby, M. B. Sporn and G. W. Gribble, Org. Biomol. Chem., 2014, 12, 5192
    DOI: 10.1039/C4OB00679H

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