A practical synthesis of betulonic acid using selective oxidation of betulin on aluminium solid support

Molecules. 2012 Oct 9;17(10):11849-63. doi: 10.3390/molecules171011849.

Abstract

The room temperature oxidation of betulin by Cr(VI) compounds in aqueous acetone on solid supports such as alumina, zeolites and silica gel has been studied. The oxidation on alumina support leaded to a single product--betulonic acid--in quantitative yield. One hundred percent selective oxidation during 30 min of betulin up to betulonic aldehyde was determined when silica gel support was used. The oxidation of betulin using zeolites as a support gives a mixture of betulonic acid and aldehyde in a 2:1 ratio. It is proposed the selective oxidation up to betulonic acid is due to the influence of Al³⁺-ions.

MeSH terms

  • Aluminum / chemistry*
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemical synthesis
  • Oxidation-Reduction
  • Solid-Phase Synthesis Techniques
  • Triterpenes / chemistry*

Substances

  • Triterpenes
  • betulonic acid
  • Oleanolic Acid
  • betulin
  • Aluminum