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Int. J. Mol. Sci. 2008, 9(1), 89-97; doi:10.3390/ijms9010089
Article

Germacrene D Cyclization: An Ab Initio Investigation

Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA
Received: 17 December 2007 / Accepted: 23 January 2008 / Published: 25 January 2008
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Abstract

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. germacrene D; cadinene; muurolene; amorphene; selinene; density functional theory; ab initio molecular orbital theory.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Setzer, W.N. Germacrene D Cyclization: An Ab Initio Investigation. Int. J. Mol. Sci. 2008, 9, 89-97.

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