Structural determination of oleanane-28,13β-olide and taraxerane-28,14β-olide fluorolactonization products from the reaction of oleanolic acid with SelectfluorTM

Abstract

The X-ray crystal structure data of 12-α-fluoro-3β-hydroxyolean-28,13β-olide methanol hemisolvate, 2C30H47FO3·CH3OH, (1), and 12-α-fluoro-3β-hydroxytaraxer-28,14β-olide methanol hemisolvate, 2C30H47FO3·CH3OH, (2), are described. The fluorolactonization of oleanolic acid using SelectfluorTM yielded a mixture of the six-membered δ-lactone (1) and the unusual seven-membered γ-lactone (2) following a 1,2-shift of methyl C-27 from C-14 to C-13.

Keywords

• crystal structure
• oleanolic acid
• fluorolactone
• selectfluor
• taraxerane
• oleanane
• triterpenoids
• lactone