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Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
J Martín Torres-Valencia1, Guadalupe I León, J Roberto Villagómez-Ibarra
1Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Hidalgo, Km. 4.5 Carretera Pachuca-Tulancingo, Unidad Universitaria, C.P. 42076 Pachuca, Hidalgo, Mexico. jmartin@uaeh.reduaeh.mx
Abstract:
A method to determine the absolute configuration of 2,3-epoxy-2-methylbutanoate ester residues in natural products is presented, based on (i) the reduction of the ester function to yield a 2-methyl-1,2-butanediol, (ii) esterification of the obtained primary alcohol with either (R)-(+)- or (S)-(-)-Mosher's acid to afford the corresponding Mosher's ester, and (iii) 1H-NMR spectral comparison of the final product with that of the Mosher's esters prepared from 2-methyl-1,2-butanediols of known stereochemistry.