Germacrene D cyclization: an Ab initio investigation.

Area of Science:

• Organic Chemistry
• Computational Chemistry
• Natural Products Chemistry

Background:

• Germacrene D is a sesquiterpene found in essential oils.
• Cadinane and selinane sesquiterpenes often co-occur with germacrene D.

Purpose of the Study:

• To computationally investigate the acid-catalyzed cyclization of germacrene D.
• To understand the formation pathways of cadinane and selinane sesquiterpenes.

Main Methods:

• Density functional theory (DFT) calculations using B3LYP/6-31G(*).
• Post-Hartree-Fock ab initio methods (MP2/6-31G(* *)).

Main Results:

• Calculated energies generally agree with experimental product distributions.
• The study provides insights into the mechanisms of sesquiterpene formation.

Conclusions:

• Computational methods can accurately predict product distributions in sesquiterpene cyclizations.
• Findings support the proposed pathways for cadinane and selinane formation from germacrene D.