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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (8), p. 164-169, 2012

DOI: 10.3762/bjoc.8.17

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Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP): A convenient 2-step procedure towards 12-oxo-28-carboxylic acid derivatives

Journal article published in 2012 by Jorge A. R. Salvador, Vânia M. Moreira ORCID, Rui M. A. Pinto, Ana S. Leal, José A. Paixão ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

A new, straightforward and high yielding procedure to convert oleanolic acid derivatives into the corresponding δ-hydroxy-γ-lactones, by using the convenient oxidizing agent magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) in refluxing acetonitrile, is reported. In addition, a two-step procedure for the preparation of oleanolic 12-oxo-28-carboxylic acid derivatives directly from Δ12-oleananes, without the need for an intermediary work-up, and keeping the same reaction solvent in both steps, is described as applied to the synthesis of 3,12-dioxoolean-28-oic acid.