Synthesis of New A-Seco-Derivatives of Methyl Glycyrrhetinate

New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H 2 O 2 (30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydr...

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Bibliographic Details
Published in:Chemistry of natural compounds 2024-07, Vol.60 (4), p.657-661
Main Authors: Karimova, E. R., Baltina, L. A., Nugumanov, T. R., Medvedeva, N. I., Spirikhin, L. V., Kukovinets, O. S.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Esters
Hydrogen peroxide
Organic Chemistry
Plant Sciences
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Summary:New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H 2 O 2 (30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydroxymethylene-3-oxo-derivative of MeGLC produced for the first time the methyl esters of 2,3-seco-2-ethoxycarbonyl- 18 βH -olean-12-ene-2,3,30-trioic acid and 2,3-anhydro-11-oxo-18 βH -olean-9,12-diene-2,3,30-trioic acid.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-024-04407-2