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Predicting NMR Spectra by Computational Methods:  Structure Revision of Hexacyclinol

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Department of Chemistry, 1102 Natural Sciences II, University of CaliforniaIrvine, Irvine, California 92697-2025
Cite this: Org. Lett. 2006, 8, 13, 2895–2898
Publication Date (Web):June 1, 2006
https://doi.org/10.1021/ol0611346
Copyright © 2006 American Chemical Society
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Abstract

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The structure of the natural product hexacyclinol was reassigned from endoperoxide 1 to the diepoxide 7 on the basis of calculated 13C chemical shift data using HF/3-21G geometries and mPW1PW91/6-31G(d,p) GIAO NMR predictions. These predictions correlate very well with experimental data for three other highly oxygenated natural products, elisapterosin B, maoecrystal V, and elisabethin A. Hexacyclinol is proposed to arise from acid-catalyzed rearrangement of panepophenanthrin in the presence of methanol.

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Calculated geometries and predicted NMR shifts are presented for the compounds discussed. This material is available free of charge via the Internet at http://pubs.acs.org.

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