STEREOCHEMISTRY OF HYDROGEN-PEROXIDE ACETIC-ACID OXIDATION OF URSOLICACID AND RELATED-COMPOUNDS

Authors
TKACHEV AV DENISOV AY GATILOV YV BAGRYANSKAYA IY SHEVTSOV SA RYBALOVA TV
Citation
Av. Tkachev et al., STEREOCHEMISTRY OF HYDROGEN-PEROXIDE ACETIC-ACID OXIDATION OF URSOLICACID AND RELATED-COMPOUNDS, Tetrahedron, 50(39), 1994, pp. 11459-11488
Citations number
69
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
39
Year of publication
1994
Pages
11459 - 11488
Database
ISI
SICI code
0040-4020(1994)50:39<11459:SOHAOO>2.0.ZU;2-2
Abstract
Stereochemistry of a number of oxidized derivatives of ursolic acid wa s established using NMR data and X-ray analysis. Full signal assignmen ts were made in H-1 and C-13 NMR spectra of 26 natural and synthetic u rsane type triterpenoids. Possible mechanisms of oxidation of ursolic acid and related compounds by peracids, as well as mechanisms of secon dary processes, were formualted basing on chemical behavior and molecu lar mechanics calculations of the starting materials and certain inter mediate species.