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

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URI: https://hdl.handle.net/10481/96624
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Autor
A. Eadsforth, Megan; Kong, Linghan; Whitehead, George F. S.; Vitorica-Yrezabal, Iñigo Javier; T. O’Keefe, Raymond; A. Bryce, Richard; C. Whitehead, Roger
Editorial
International Union of Crystallography
Materia
crystal structure
 
oleanolic acid
 
fluoro­lactone
 
Fecha
2024-08
Referencia bibliográfica
A. Eadsforth, M. et. al. Acta Cryst. (2024). E80, 857–862. [https://doi.org/10.1107/S2056989024006480]
Patrocinador
Biotechnology and Biological Sciences Research Council (studentship No. 2110646 to Megan A Eadsforth; grant No. BB/S00047X/1
Resumen
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.
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