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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biological Factors / chemistry*
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Biological Factors / metabolism
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Butylene Glycols / chemistry*
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Butylene Glycols / isolation & purification
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Butyrates / chemistry*
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Butyrates / isolation & purification
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Epoxy Compounds / chemistry*
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Epoxy Compounds / isolation & purification
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Magnetic Resonance Spectroscopy / methods
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Molecular Conformation
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Phenylacetates / chemistry
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Spectrophotometry, Infrared
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Terpenes / chemistry*
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Terpenes / isolation & purification
Substances
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Biological Factors
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Butylene Glycols
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Butyrates
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Epoxy Compounds
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Phenylacetates
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Terpenes
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2-methyl-1,2-butanediol
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Mosher's acid