Stereoselective Epoxidation of Triterpenic Allylic Alcohols and Cytotoxicity Evaluation of Synthesized Compounds.

ABSTRACT: The epoxidation process of semi-synthetic triterpenoids 2-methyl-3-oxo-19β,28-epoxy- 18α-olean-1-ene, and its allylic alcohol derivatives were examined. 1,2α-epoxide, as the main product, was found to be formed from the starting enone exposed to m-chloroperbenzoic acid (mCPBA). In the case of hydroxy-directed mCPBA-oxidation of triterpenic allyl alcohols and their 3α-alkyl-substituted derivatives, inversion of C1 and C2 asymmetric centers with the formation of 1,2β-epoxyalcohols took place. The synthesis of 2,3α-epoxides was fulfilled from 2,3-dialkyl-substituted C(3) allyl alcohols by the action of pyridinium chlorochromate under [1,3]-oxidative rearrangement conditions. The transformations brought about enabled chiral oleanane derivatives with an oxygen-containing substituent at t

SUBMITTER: Krainova G 

PROVIDER: S-EPMC9863255 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature