title: Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters.
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.
authors.affiliation: 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
authors.forename: J Martín
authors.initials: JM
authors.lastname: Torres-Valencia
authors.forename: Guadalupe I
authors.initials: GI
authors.lastname: León
authors.forename: J Roberto
authors.initials: JR
authors.lastname: Villagómez-Ibarra
authors.forename: Oscar R
authors.initials: OR
authors.lastname: Suárez-Castillo
authors.forename: Carlos M
authors.initials: CM
authors.lastname: Cerda-García-Rojas
authors.forename: Pedro
authors.initials: P
authors.lastname: Joseph-Nathan
mesh_terms: 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
chemical_list: 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