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Issue 41, 2015
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The energetic viability of an unexpected skeletal rearrangement in cyclooctatin biosynthesis

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Abstract

Results of density functional theory calculations on possible mechanisms for formation of the diterpenoid cyclooctatin are described. These results are consistent with the involvement of an unexpected 1,3-alkyl shift that interconverts two cyclopropylcarbinyl carbocations and interchanges the positions of two carbon atoms in an 8-membered ring. Predictions for future experiments to provide further support of this mechanism also are described.

Graphical abstract: The energetic viability of an unexpected skeletal rearrangement in cyclooctatin biosynthesis

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Publication details

The article was received on 26 Aug 2015, accepted on 09 Sep 2015 and first published on 10 Sep 2015


Article type: Communication
DOI: 10.1039/C5OB01785H
Citation: Org. Biomol. Chem., 2015,13, 10273-10278
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    The energetic viability of an unexpected skeletal rearrangement in cyclooctatin biosynthesis

    Y. J. Hong and D. J. Tantillo, Org. Biomol. Chem., 2015, 13, 10273
    DOI: 10.1039/C5OB01785H

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