Title

Oxidative lactonization of oleanane and ursane acids by treating with ozone.

Authors

Husnutdinova, E.; Lobov, A.; Kukovinets, O.; Kataev, V.; Kazakova, O.

Abstract

Features of process of oxidative lactonization of 3-oxooleanolic and 3-oxoursolic acids under treatment with ozone were established. The similarity of the processes consists in generation of 3-oxooleanolic or 3-oxoursolic 13β,28-lactones with 12-oxo or 12-hydroxy group. In the case of ursane derivative the generation exclusively of compounds with β-oriented 12-hydroxy group was observed, in the case of oleanane lactones prevailingly compounds with α-oriented 12-hydroxy group were obtained. The processes differ by the generation of the product of allylic oxidation, 3,11-dioxoursolic acid, or the isolation of the product of the lactone cycle opening with participation of the solvent, 3,12-dioxoolean-28-olic acid.

Subjects

LACTONES; ORGANIC cyclic compounds; HYDROXY acids; OXIDATION; MACROCYCLIC compounds; ORGANIC chemistry

Publication

Russian Journal of Organic Chemistry, 2015, Vol 51, Issue 2, p261

ISSN

1070-4280

Publication type

Academic Journal

DOI

10.1134/S1070428015020219