Protonated montmorillonite-mediated highly specific isomerization of oleanolic acid esters: application to the synthesis of Δ13(18)-CDDO-Me?

Organic & Biomolecular Chemistry Pub Date: 2016-11-02 DOI: 10.1039/C6OB02126C

Abstract

A one-pot highly specific isomerization of oleanolic acid esters (5a–g) to δ-oleanolic acid esters (6a–g) was achieved in the presence of proton-exchanged montmorillonite (H-mont) under mild reaction conditions. This protocol could proceed smoothly on a 15.0 gram scale. Based on this methodology, the synthesis of the biologically active compound Δ13(18)-CDDO-Me (4) was realized.

Graphical abstract: Protonated montmorillonite-mediated highly specific isomerization of oleanolic acid esters: application to the synthesis of Δ13(18)-CDDO-Me
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