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Oxidation of Licorice-Root Triterpene-Acid Derivatives by m-Chloroperbenzoic Acid

Author:
Mikhailova, L. R., Budaev, A. S., Spirikhin, L. V., Baltina, L. A.
Source:
Chemistry of natural compounds 2019 v.55 no.1 pp. 88-91
ISSN:
0009-3130
Subject:
acids, chemical structure, esters, licorice, nuclear magnetic resonance spectroscopy, oxidation
Abstract:
Methyl esters of 3β-O-acetoxy-18βH-olean-12-en-30-oic, 3β-hydroxy-9(11),12(13)-dien-30-oic, and 3β-O-acetoxy-18βH-olean-12-en-30-oic acids were oxidized by meta-chloroperbenzoic acid (m-CPBA) to produce methyl esters of 3β-O-acetoxy-12α,13α-epoxy-18β-oleanan-30-oic and 3β-O-acetoxy-18β-oleanan-12-on-30-oic acids in addition to 3β-hydroxy-12-oxo-18βH-olean-9(11)-en-30-oic and 3β-O-acetoxy-18β-oleanan-12-on-30-oic acids in 70–75% yields. The structures of the synthesized compounds were confirmed by PMR and ¹³C NMR spectra.
Agid:
6332307