Structural elucidation of absolute configurations of the stereogenic centers of acetogenins of Annonaceae was performed using the modified Mosher's method. Thus, by replacing MTPA (methoxytrifluoromethylphenylacetic acid) by 2-NMA (naphthylmethoxyacetic acid), we were able to determine the absolute configuration of the stereogenic centers of rolliniastatin-2 by simple analysis of the 1 H NMR spectra recorded at 400 MHz. Indeed, by comparing the differences of chemical shifts between the MTPA esters with those obtained with 2-NMA esters, we showed that we could take advantage of the long-range anisotropic effect of the naphthyl ring for the elucidation of the unsymmetrical systems.
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Duret et al. (1998) studied this question.
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