Phytochemical Analysis 2002-01-01

Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters.

J Martín Torres-Valencia, Guadalupe I León, J Roberto Villagómez-Ibarra, Oscar R Suárez-Castillo, Carlos M Cerda-García-Rojas, Pedro Joseph-Nathan

Index: Phytochem. Anal. 13(6) , 329-32, (2002)

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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.