The absolute configuration of cuauhtemone and related compounds

The absolute configuration 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 st...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2003-03, Vol.14 (5), p.543-548
Main Authors: Torres-Valencia, J.Martı́n, Quintero-Mogica, Dora L., León, Guadalupe I., Suárez-Castillo, Oscar R., Villagómez-Ibarra, J.Roberto, Maldonado, Emma, Cerda-Garcı́a-Rojas, Carlos M., Joseph-Nathan, Pedro
Format: Article
Language:English
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Summary:The absolute configuration 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 absolute configurations of a relevant group of natural products, which were elucidated according to the stereochemistry of cuauhtemone. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(03)00042-9