The absolute configuration of cuauhtemone and related compounds. Torres-Valencia J. M., Quintero-Mogica D. L., León G. I., Suárez-Castillo O. R., Villagómez-Ibarra J. R., Maldonado E., Cerda-García-Rojas C. M., Joseph-Nathan P. DOI: http://dx.doi.org/10.1016/S0957-4166(03)00042-9
The absoluteconfiguration of cuauhtemone, a eudesmane-type sesquiterpene isolated from Pluchea species (Asteraceae), has been revised from 1 to 2 by chemical correlation with (R)-(+)-2-methyl-1,2-butanediol 3 through the naturally occurring 2,3-epoxy-2-methylbutanoate derivative 4. The relative stereochemistry of 4 was confirmed by X-ray diffraction analysis. The obtained data are also useful for reconsideration of the absoluteconfigurations of a relevant group of natural products, which were elucidated according to the stereochemistry of cuauhtemone.