Journal
ORGANIC LETTERS
Volume 8, Issue 13, Pages 2895-2898Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0611346
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- NIGMS NIH HHS [GM-43854] Funding Source: Medline
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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 C-13 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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