Synthesis of norhydroperoxides from natural triterpenic acids Full article
| Journal |
Collection of Czechoslovak Chemical Communications
ISSN: 0010-0765 |
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| Output data | Year: 2001, Volume: 66, Number: 12, Pages: 1753-1763 Pages count : DOI: 10.1135/cccc20011753 | ||||
| Tags | NMR spectroscopy; Michael additions; peroxides; mercury; terpenoids; triterpenes; oxidations; decarboxylations | ||||
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Abstract:
Treatment of triterpenoids derived from ursolic and glycyrrhetinic acids with the oxidative mixture H2O2-(CF3COO)(2)Hg-Na2CO3-THF results in oxidative decarboxylation. The reaction of 3O-acetylursolic acid (1) and 3O-acetyl-18beta-glycyrrhetinic acid (3) affords stable norhydroperoxides, whereas decarboxylation of 30-acetyl-11-oxoursolic acid (6) 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.
Cite:
Tatarov E.
, Tkachev A.
Synthesis of norhydroperoxides from natural triterpenic acids
Collection of Czechoslovak Chemical Communications. 2001. V.66. N12. P.1753-1763. DOI: 10.1135/cccc20011753 WOS Scopus РИНЦ OpenAlex
Synthesis of norhydroperoxides from natural triterpenic acids
Collection of Czechoslovak Chemical Communications. 2001. V.66. N12. P.1753-1763. DOI: 10.1135/cccc20011753 WOS Scopus РИНЦ OpenAlex
Identifiers:
| Web of science: | WOS:000173678600004 |
| Scopus: | 2-s2.0-23044534290 |
| Elibrary: | 13383230 |
| OpenAlex: | W2950574752 |