Predicting NMR Spectra by
Computational Methods: Structure
Revision of Hexacyclinol
Scott D. Rychnovsky*
Department of Chemistry, 1102 Natural Sciences II, University of California-Irvine,
Irvine, California 92697-2025
srychnov@uci.edu
Received May 9, 2006
Abstract:
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.
