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Issue 5, 1970
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Conversion of α- and β-amyrin into ursolic and oleanolic acids respectively. A synthesis of oleanolic acid

Abstract

β-Amyrin has been converted into 3β-acetoxy-13-hydroxyoleanane. Photolysis of the nitrite of this alcohol and further standard transformations gave oleanolic acid lactone acetate and thence oleanolic acid. This conversion of β-amyrin into oleanolic acid represents, in the formal sense, a total synthesis of the latter.

By a similar series of reactions ursolic acid has been obtained from α-amyrin.

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Article information


J. Chem. Soc. C, 1970, 678-682
Article type
Paper

Conversion of α- and β-amyrin into ursolic and oleanolic acids respectively. A synthesis of oleanolic acid

R. B. Boar, D. C. Knight, J. F. McGhie and D. H. R. Barton, J. Chem. Soc. C, 1970, 678
DOI: 10.1039/J39700000678

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