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


ABSTRACT: The X-ray crystal structure data of 12-α-fluoro-3β-hy-droxy-olean-28,13β-olide methanol hemisolvate, 2C30H47FO3·CH3OH, (1), and 12-α-fluoro-3β-hy-droxy-taraxer-28,14β-olide methanol hemisolvate, 2C30H47FO3·CH3OH, (2), are described. The fluoro-lactonization 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.

SUBMITTER: Eadsforth MA 

PROVIDER: S-EPMC11299754 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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

Eadsforth Megan A MA   Kong Linghan L   Whitehead George G   Vitórica-Yrezábal Iñigo J IJ   O'Keefe Raymond T RT   Bryce Richard A RA   Whitehead Roger C RC  

Acta crystallographica. Section E, Crystallographic communications 20240715 Pt 8


The X-ray crystal structure data of 12-α-fluoro-3β-hy-droxy-olean-28,13β-olide methanol hemisolvate, 2C<sub>30</sub>H<sub>47</sub>FO<sub>3</sub>·CH<sub>3</sub>OH, (<b>1</b>), and 12-α-fluoro-3β-hy-droxy-taraxer-28,14β-olide methanol hemisolvate, 2C<sub>30</sub>H<sub>47</sub>FO<sub>3</sub>·CH<sub>3</sub>OH, (<b>2</b>), are described. The fluoro-lactonization of oleanolic acid using Selectfluor<sup>TM</sup> yielded a mixture of the six-membered δ-lactone (<b>1</b>) and the unusual seven-membered γ  ...[more]

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