The epoxidation (H2O2, NaOH) of an acetonyl-cycloheptenone derived from (R)-(-)-carvone gives a dihydroxy-nor-guaiane sesquiterpene by way of an interesting sequence of reactions promoted by the basic reaction conditions. Although the major product could be identified spectroscopically with respect to functional groups, its complete three dimensional structure was determined by X-ray mono-crystal diffraction studies.
nor-guaiane sesquiterpene; epoxidation; intramolecular aldol; beta,gamma-epoxy-ketone rearrangement; X-ray analysis
