Predicting NMR spectra by computational methods: Structure revision of hexacyclinol

Organic Letters

Volumn 8, Issue 13, 2006, Pages 2895-2898

  Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; EPOXIDE; HEXACYCLINOL; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE;

BIOLOGICAL PRODUCTS; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; POLYCYCLIC COMPOUNDS;

EID: 33746115758     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0611346     Document Type: Article

References (25)

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13. Spartan 04 for Macintosh; Wavefunction Inc.: Irvine, CA.
14. The Gaussian 03 reference is included in the Supporting Information.
15. The linux computer incorporated a 3.06 GHz Pentium 4 processor.
16. The slopes (0.9540, 0.9604, 0.9681) and intercepts (2.11, 2.06, 1.84) for elisapterosin B, maoecrystal V, and elisabethin A, respectively, are all very similar. Full details can be found in the Supporting Information.
17. Sekizawa, R.; Ikeno, S.; Nakamura, H.; Naganawa, H.; Matsui, S.; Iinuma, H.; Takeuchi, T. J. Nat. Prod. 2002, 65, 1491-1493.
18. Syntheses of panepophenanthrin: (a) Moses, J. E.; Commeiras, L.; Baldwin, J. E.; Adlington, R. M. Org. Lett. 2003, 5, 2987-2988.
19. (b) Lei, X.; Johnson, R. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2003, 42, 3913-3917.
20. (c) Mehta, G.; Islam, K. Tetrahedron Lett. 2004, 45, 7683-7687.
21. (d) Mehta, G.; Ramesh, S. S. Tetrahedron Lett. 2004, 45, 1985-1987.
22. The carbon numbers for structures 6 and 7 correspond to the carbon numbers reported for hexacyclinol, which simplifies comparison with the experimental NMR data.
23. 13C chemical shift analysis was performed on the other three stereoisomers of 6, but the correlations were inferior to that of compound 7. Details are provided in the Supporting Information.
24. These two peaks were reported at 3.65 and 3.62 ppm in the German patent: Schlegel, B.; Härtle, A.; Dahse, H.-M.; Gollmick, F. A.; Gräfe, U.; Dörfelt, H. DE 10213481 A1.
25. Porco prepared a closely related structure (diketone 24 in ref 15b) as part of his elegant synthetic approach to panepophenanthrin. The spectra of Porco's compound 24 and hexacyclinol show the expected similarities. The C18 proton shows a 2.4 Hz allylic coupling with C9, as was observed for hexacyclinol.