Predicting NMR spectra by computational methods: Structure revision of hexacyclinol

被引：159
|
作者：
Rychnovsky, Scott D. [1 ]
机构：
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 13期
关键词：
D O I：
10.1021/ol0611346
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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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收藏
页码：2895 / 2898
页数：4
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