Issue 41, 2015
From the journal:

Organic & Biomolecular Chemistry

The energetic viability of an unexpected skeletal rearrangement in cyclooctatin biosynthesis†

Young J. Honga  and  Dean J. Tantillo*a  

* Corresponding authors

a Department of Chemistry, Univeristy of California-Davis, Davis, CA 95616, USA
E-mail: djtantillo@ucdavis.edu

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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Article information

DOI
https://doi.org/10.1039/C5OB01785H
Article type
Communication
Submitted
26 Aug 2015
Accepted
09 Sep 2015
First published
10 Sep 2015

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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