Methanolysis or sodium borohydride reduction of the 3-acetoxy-7,19-dimethyl ester of gibberellin A13 20-toluene-p-sulphonyl anhydride afforded, respectively, the unusual 19-orthoester or epimeric 19-acetals as the major products rather than the products of simple displacement of the 20-toluene-p-sulphonoxy-group. The structure of the 19-orthoester was proven by X-ray analysis.
B. M. Fraga, A. G. Gonzalez, M. G. Hernandez, F. G. Tellado, J. R. Hanson and P. B. Hitchcock, J. Chem. Soc., Perkin Trans. 1, 1981, 2740 DOI: 10.1039/P19810002740
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