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

Phytochem Anal. Nov-Dec 2002;13(6):329-32. doi: 10.1002/pca.652.

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

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Factors / chemistry*
  • Biological Factors / metabolism
  • Butylene Glycols / chemistry*
  • Butylene Glycols / isolation & purification
  • Butyrates / chemistry*
  • Butyrates / isolation & purification
  • Epoxy Compounds / chemistry*
  • Epoxy Compounds / isolation & purification
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Conformation
  • Phenylacetates / chemistry
  • Spectrophotometry, Infrared
  • Terpenes / chemistry*
  • Terpenes / isolation & purification

Substances

  • Biological Factors
  • Butylene Glycols
  • Butyrates
  • Epoxy Compounds
  • Phenylacetates
  • Terpenes
  • 2-methyl-1,2-butanediol
  • Mosher's acid