Summary and Valuation

The aim of this work was to develop the main constituents of essential oils, in this case monoterpene ketones (menthone and pulegone). The aim was twofold: to develop the preparative aspect of the reactions without neglecting the application of the synthesized products. The first objective was met by obtaining different series of p-menthan derivatives of potential interest in organic synthesis. As a result, we obtained p-menthan alcohols with three to four asymmetric centers of well-defined configuration. Indeed, we have shown that the action of allylic, aromatic and saturated organomagnesiums on menthone leads stereoselectively to p-menthan-3-ol derivatives with axial hydroxyl groups. Condensation of the same magnesium series with pulegone produces the corresponding alcohols with equatorial hydroxyl groups. Still using menthone, we observed the stereoselective formation of epoxides by the action of m-chloroperbenzoic acid on 3-allyl-p-menthan-3-ols, which may be the starting point for the preparation of heterocycles.