Stereochemical assignment of naturally occurring 2,3‐epoxy‐2‐methylbutanoate esters
2002; Wiley; Volume: 13; Issue: 6 Linguagem: Inglês
10.1002/pca.652
ISSN1099-1565
AutoresJ. Martín Torres‐Valencia, Guadalupe I. León, José Roberto Villagómez‐Ibarra, Oscar R. Suárez‐Castillo, Carlos M. Cerda‐García‐Rojas, Pedro Joseph‐Nathan,
Tópico(s)Phosphorus compounds and reactions
ResumoA 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.
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