The absolute configuration of cuauhtemone and related compounds

✍ Scribed by J.Martı́n Torres-Valencia; Dora L. Quintero-Mogica; Guadalupe I. León; Oscar R. Suárez-Castillo; J.Roberto Villagómez-Ibarra; Emma Maldonado; Carlos M. Cerda-Garcı́a-Rojas; Pedro Joseph-Nathan

• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 230 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00042-9

✦ Synopsis

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.