International Journal of Molecular Sciences, Vol.9, No.1, 89-97, 2008
Germacrene D cyclization: An Ab initio investigation
Essential oils that contain large concentrations of germacrene D are typically accompanied by cadinane sesquiterpenoids. The acid-catalyzed cyclization of germacrene D to give cadinane and selinane sesquiterpenes has been computationally investigated using both density functional (B3LYP/6-31G*) and post Hartree-Fock (MP2/6-31G**) ab initio methods. The calculated energies are in general agreement with experimentally observed product distributions, both from acid-catalyzed cyclizations as well as distribution of the compounds in essential oils.
Keywords:germacrene D;cadinene;muurolene;amorphene;selinene;density functional theory;ab initio molecular orbital theory