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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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