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.
引用
收藏
页码：2895 / 2898
页数：4
相关论文
共 50 条
  • [41] COMPUTATIONAL STUDY OF MOLECULAR STRUCTURE, 1H NMR, ELECTRONIC SPECTRA, SOLVENT EFFECT AND PROPERTIES OF PLATINABENZENE
    Ghiasi, Reza
    Ghiasi, Hossein
    Tabar, Mahsan Afzal
    REVUE ROUMAINE DE CHIMIE, 2014, 59 (09) : 749 - 760
  • [42] Automated structure determination from NMR spectra
    Peter Güntert
    European Biophysics Journal, 2009, 38 : 129 - 143
  • [43] INTERPRETATION OF MOLECULAR STRUCTURE FROM NMR SPECTRA
    ZSCHUNKE, A
    PHARMAZIE, 1969, 24 (09): : 577 - &
  • [44] NMR-SPECTRA AND STRUCTURE OF ORGANOMERCURY COMPOUNDS
    PETROSYAN, VS
    REUTOV, OA
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 76 (02) : 123 - 169
  • [45] Pattern recognition of the multiplet structure of NMR spectra
    Golotvin, SS
    Chertkov, VA
    RUSSIAN CHEMICAL BULLETIN, 1997, 46 (03) : 423 - 430
  • [46] ON THE STRUCTURE OF WATER NMR-SPECTRA IN MEMBRANES
    MANK, VV
    LEBOVKA, NI
    CHEMICAL PHYSICS LETTERS, 1983, 96 (06) : 626 - 630
  • [47] Computational modeling structure and spectra of biological chromophores
    Collins, Jack R.
    Topol, Igor A.
    Nemukhin, Alexander V.
    Savitsky, Alexander P.
    FLUORESCENCE IN VIVO IMAGING BASED ON GENETICALLY ENGINEERED PROBES: FROM LIVING CELLS TO WHOLE BODY IMAGING IV, 2009, 7191
  • [48] NMR SPECTRA YEILD DATA ON PROTEIN STRUCTURE
    不详
    PHYSICS TODAY, 1968, 21 (09) : 74 - &
  • [49] Computational Methods for Predicting Sites of Functionally Important Dynamics
    Schuyler, Adam D.
    Carlson, Heather A.
    Feldman, Eva L.
    JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (19): : 6613 - 6622
  • [50] Computational methods for predicting genomic islands in microbial genomes
    Lu, Bingxin
    Leong, Hon Wai
    COMPUTATIONAL AND STRUCTURAL BIOTECHNOLOGY JOURNAL, 2016, 14 : 200 - 206
12345