Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP)

Jorge A. R. Salvador, Vânia M. Moreira, Rui M. A. Pinto, Ana S. Leal, José A. Paixão

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)164-169
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume8
DOIs
Publication statusPublished - 30 Jan 2012

Keywords

  • triterpenoid
  • oleanolic acid
  • bismuth(III) triflate

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