Phytochemical Analysis 2002-01-01

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

J Martín Torres-Valencia, Guadalupe I León, J Roberto Villagómez-Ibarra, Oscar R Suárez-Castillo, Carlos M Cerda-García-Rojas, Pedro Joseph-Nathan

Index: Phytochem. Anal. 13(6) , 329-32, (2002)

Full Text: HTML

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.

Related Compounds

  • Mosher's acid
  • 2,3-DICHLOROB...
  • (R)-(+)-Mosher's...

Related Articles:

[Three dimensional structure analysis of organic chemical compounds from natural sources using NMR spectral analysis].

2003-01-01

[Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho. Hokoku. (121) , 87-8, (2003)]

Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.

2007-01-01

[Nat. Protoc. 2 , 2451-2458, (2007)]

Neural systems of reinforcement for drug addiction: from actions to habits to compulsion.

2005-11-01

[Nat. Neurosci. 8(11) , 1481-9, (2005)]

Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers.

2010-05-07

[J. Org. Chem. 75(9) , 2942-54, (2010)]

Long-range shielding effects in the (1)H NMR spectra of Mosher-like ester derivatives.

2010-04-16

[Org. Lett. 12(8) , 1768-71, (2010)]

More Articles...