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

Dongyin Chen; Pu Zhang; Yan Sun; Pengfei Wang; Can Zhang; Lingyi Kong; Ji Zhang; Hongbin Sun; Xiaoan Wen

doi:10.1039/C6OB02126C

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

Dongyin Chen,‡^ac Pu Zhang,‡^a Yan Sun,‡^a Pengfei Wang,^a Can Zhang,^a Lingyi Kong,^a Ji Zhang,*^b Hongbin Sun*^a and Xiaoan Wen*^a

Author affiliations

* Corresponding authors

^a Jiangsu Key Laboratory of Drug Discovery for Metabolic Disease and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing 210009, China
E-mail: hongbinsun@cpu.edu.cn, wxagj@126.com

^b Department of Physical Chemistry, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing 210009, China
E-mail: jzhangcpu@126.com

^c Department of Medicinal Chemistry, School of Pharmacy, Nanjing Medical University, 101 Longmian Avenue, Nanjing 211166, China

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.

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Article information

DOI: https://doi.org/10.1039/C6OB02126C
Article type: Paper
Submitted: 29 Sep 2016
Accepted: 01 Nov 2016
First published: 02 Nov 2016

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Org. Biomol. Chem., 2016,14, 11154-11161

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

D. Chen, P. Zhang, Y. Sun, P. Wang, C. Zhang, L. Kong, J. Zhang, H. Sun and X. Wen, Org. Biomol. Chem., 2016, 14, 11154 DOI: 10.1039/C6OB02126C

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Organic & Biomolecular Chemistry