Producción Científica Profesorado

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



Suárez Castillo, Oscar Rodolfo

2002

Stereochemical assignment of natural occurring 2,3-epoxy-2-methylbutanoate esters. J. Martín Torres-Valencia, Guadalupe I. León, J. Roberto Villagómez-Ibarra, Oscar R. Suárez-Castillo, Carlos Cerda-García-Rojas, Pedro Joseph-Nathan. 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.



Producto de Investigación




Artículos relacionados

Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase

Synthesis of ?4:?2-Exocyclic-Diene Iridium(I) Complexes Derived from 1,3-Oxazolidin-2-ones and Their...

The absoluteconfiguration of cuauhtemone and related compounds

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural ...

Transesterifications mediated by t-BuNH2

Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling

Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea

Conformationalstudies of N-carbomethoxy-2-alkoxyindolenines by dynamic NMR, crystallography, and mol...