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

Megan Eadsforth, Linghan Kong, George Whitehead, Iñigo J. Vitorica-Yrezabal, Raymond O'Keefe, Richard Bryce, Roger Whitehead

Research output: Contribution to journalArticlepeer-review

Abstract

The X-ray crystal structure data of 12-α-fluoro-3β-hydroxyolean-28,14-β-olide methanol solvate, 2(C30H47FO3)·CH4O, (1), and 12-α-fluoro-3β-hydroxytaraxer-28,13-β-olide methanol solvate, C30H47FO3·0.5(CH4O), (2), are described. Thefluorolactonisation of oleanolic acid using SelectfluorTM yielded a mixture of the 6-membered δ-lactone (1) and theunusual 7-membered γ-lactone (2) following a 1,2-shift of methyl C-27 from C-14 to C-13.
Original languageEnglish
JournalActa Crystallographica Section E
Publication statusAccepted/In press - 24 Jun 2024

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