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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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Submitted
26 Aug 2015
Accepted
09 Sep 2015
First published
10 Sep 2015

Org. Biomol. Chem., 2015,13, 10273-10278
Article type
Communication

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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