Structural determination of oleanane-28,13β-olide and taraxerane-28,14β-olide fluoro-lactonization products from the reaction of oleanolic acid with Selectfluor(TM).

通过齐墩果酸与 Selectfluor(TM) 的反应,确定齐墩果烷-28,13β-内酯和蒲公英烷-28,14β-内酯氟化产物的结构

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作者:Eadsforth Megan A, Kong Linghan, Whitehead George, Vitórica-Yrezábal Iñigo J, O'Keefe Raymond T, Bryce Richard A, Whitehead Roger C
The X-ray crystal structure data of 12-α-fluoro-3β-hy-droxy-olean-28,13β-olide methanol hemisolvate, 2C(30)H(47)FO(3)·CH(3)OH, (1), and 12-α-fluoro-3β-hy-droxy-taraxer-28,14β-olide methanol hemisolvate, 2C(30)H(47)FO(3)·CH(3)OH, (2), are described. The fluoro-lactonization of oleanolic acid using Selectfluor(TM) 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.

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