Structural determination of oleanane-28,13β-olide and taraxerane-28,14β-olide fluoro-lactonization products from the
Megan A Eadsforth1, Linghan Kong2, George Whitehead1
1Department of Chemistry, University of Manchester, Manchester, United Kingdom.
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.
More Related Videos
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
08:43Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Related Concept Videos
Sharpless Epoxidation
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
