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Experimental and theoretical analysis of the reactivity and regioselectivity in esterification reactions of diterpenes (totaradiol, totaratriol, hinikione and totarolone)

Mohammed Zoubir, Abdellah Zeroual, Mohammed El Idrissi, Fatima Bkiri, Ahmed Benharref, Noureddine Mazoir, Abdeslam El Hajbi


Six esters have been synthesized in the acetylation, benzoylation and Baeyer-Villiger oxidation of starting materials totaradiol 1, totaratriol 2, hinikione 7 and totarolone 8. A complete theoretical study of the reaction has been carried out including highly regioselectivity induction experiments and using density functional methods B3LYP/6-31G(d). The analysis of the nucleophilic Parr functions P - k and the electrostatic potential in diterpenes 1 and 2 offered an explanation of the regioselectivity found in these reactions and in Baeyer-Villiger reaction we use transition state theory and the electrostatic potential to understand the high regioselectevity observed, we found that the regioselectivity is kinetically and thermodynamically favorable and the electronic density is located in the multi-substituted carbon.

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