Synthesis of A-nor- and A-cleaved derivatives of glycyrrhetinic acid esters by ozonolysis.

Authors

Elza Karimova, Timur Nugumanov, Svetlana Petrova, Lidia Baltina

Published in

Natural product research. Pages 1-7. Jun 19, 2026. Epub Jun 19, 2026.

Abstract

Using ozonolysis reaction, skeletal transformations of ring A of glycyrrhetinic acid methyl and butyl esters were carried out, and novel A-nor- and A-cleaved derivatives with the additional oxygen-containing functional groups have been synthesised. The main product of ozonolysis of methyl 3-(2-isopropenyl)-11-oxo-A-neo-5α,18βH-olean-12-en-30-oate was methyl 3,11-dioxo-A-nor-5βH,18βH-olean-12-ene-30-oate 4 (54%), and the minor products were methyl esters of 3,11-dioxo-5β-hydroxy-A-nor-18βH-olean-12-ene-30-oic acid 5 (10%) and 3-carboxy-5β-hydroxy-11-oxo-3,5-seco-18βH-olean-12-ene-30-oic acid 6 (12%). Butyl 3,11-dioxo-A-nor-5βH,18βH-olean-12-ene-30-oate 8 have been synthesised by ozonolysis reaction too. Structures of obtained compounds were established by high-resolution NMR spectroscopy with two-dimensional correlation (COSY, HSQC, HMBC, NOESY, HSQCED) and full assignment of protons and carbon atoms.

PMID:
42319989
Bibliographic data and abstract were imported from PubMed on 20 Jun 2026.

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