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Complete assignment of the 1H and 13C NMR spectra of garciniaphenone and keto-enol equilibrium statements for prenylated benzophenones

✍ Scribed by Priscilla B. M. C. Derogis; Felipe T. Martins; Thiago C. de Souza; Maria E. de C. Moreira; José D. Souza Filho; Antonio C. Doriguetto; Kamila R. D. de Souza; Marcia P. Veloso; Marcelo H. Dos Santos

Book ID
102527747
Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
120 KB
Volume
46
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

This article reports the structural elucidation by IR, UV and MS spectroscopic data along with ^1^H and ^13^C NMR chemical shift assignments of two benzophenones isolated from the fruit pericarp of Garcinia brasiliensis Mart. (Clusiaceae): garciniaphenone, (1__R__,5__S__,7__S__)‐3‐benzoyl‐4‐hydroxy‐6,6‐dimethyl‐5,7‐di(3‐methyl‐2‐butenyl)bicyclo[3.3.1]non‐3‐ene‐2,9‐dione, a novel triprenylated benzophenone; and 7‐epi‐clusianone, a tetraprenylated benzophenone that has already been extracted from another species of the same family. Furthermore, the keto‐enol tautomeric equilibrium at solution‐state was described for these compounds by 1D and 2D NMR spectral methods and one attempt to rationalize the different ratios between the noted tautomers was based on stereochemical features. Copyright © 2008 John Wiley & Sons, Ltd.

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