Synthesis of Norhydroperoxides from Natural Triterpenic Acids

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Title:Synthesis of Norhydroperoxides from Natural Triterpenic Acids
Creators:
Tatarov, Eugene S.
Tkachev, Alexey V.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 12, pp. 1753-1763
Uncontrolled Keywords:Decarboxylations, Mercury, Michael additions, Triterpenes, Peroxides, Oxidations, Terpenoids, NMR spectroscopy

Abstract

Treatment of triterpenoids derived from ursolic and glycyrrhetinic acids with the oxidative mixture H<sub>2</sub>O<sub>2</sub>-(CF<sub>3</sub>COO)<sub>2</sub>Hg-Na<sub>2</sub>CO<sub>3</sub>-THF results in oxidative decarboxylation. The reaction of 3<i>O</i>-acetylursolic acid (<strong>1</strong>) and 3<i>O</i>-acetyl-18β-glycyrrhetinic acid (<strong>3</strong>) affords stable norhydroperoxides, whereas decarboxylation of 3<i>O</i>-acetyl-11-oxoursolic acid (<strong>6</strong>) leads to unstable norhydroperoxide. The difference in properties of the norhydroperoxides is explained by the presence of a conjugated ketone, which activates the 12,13-C=C double bond for nucleophilic addition and makes possible intramolecular Michael-type addition of peroxo anion. <p>

Title:Synthesis of Norhydroperoxides from Natural Triterpenic Acids
Creators:
Tatarov, Eugene S.
Tkachev, Alexey V.
Uncontrolled Keywords:Decarboxylations, Mercury, Michael additions, Triterpenes, Peroxides, Oxidations, Terpenoids, NMR spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:66
Number:12
Page Range:pp. 1753-1763
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20011753UNSPECIFIED
ID Code:1893
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Tatarov, Eugene S.; Tkachev, Alexey V. (2001) Synthesis of Norhydroperoxides from Natural Triterpenic Acids. Collection of Czechoslovak Chemical Communications, 66 (12). pp. 1753-1763. ISSN 0010-0765

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