Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters.
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.
Torres-Valencia
J Martín
JM
Centro 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
León
Guadalupe I
GI
Villagómez-Ibarra
J Roberto
JR
Suárez-Castillo
Oscar R
OR
Cerda-García-Rojas
Carlos M
CM
Joseph-Nathan
Pedro
P
D001685:Biological Factors / Q000737:chemistry* / Q000378:metabolism; D002072:Butylene Glycols / Q000737:chemistry* / Q000302:isolation & purification; D002087:Butyrates / Q000737:chemistry* / Q000302:isolation & purification; D004852:Epoxy Compounds / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008968:Molecular Conformation; D010648:Phenylacetates / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification
D001685:Biological Factors; D002072:Butylene Glycols; D002087:Butyrates; D004852:Epoxy Compounds; D010648:Phenylacetates; D013729:Terpenes; C473202:2-methyl-1,2-butanediol; C108322:Mosher's acid