An efficient semi-synthesis and structure revision of a cytotoxic triterpenoid 25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid from Liquidamber styraciflua

J Asian Nat Prod Res. 2008 Mar-Apr;10(3-4):297-305. doi: 10.1080/10286020701766539.

Abstract

An efficient partial synthesis of 25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1), starting from oleanolic acid (2), has been developed in an efficient manner (13 steps, 21% yield), employing a photochemical reaction of nitrite 8 for the introduction of C-25 substituting group as the key step. Based on the comparison of its spectral data with those reported for compound 1 isolated from Liquidamber styraciflua, we found the structure in that paper was incorrectly assigned, and should be revised as 3alpha-acetoxy-25-hydroxyolean-12-en-28-oic acid (15).

MeSH terms

  • Liquidambar / chemistry*
  • Magnetic Resonance Spectroscopy
  • Nitrogen Oxides / chemistry
  • Oleanolic Acid / chemical synthesis*
  • Oleanolic Acid / chemistry
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Nitrogen Oxides
  • Oleanolic Acid
  • nitrosyl chloride