Connecting discrete stereoclusters by using DFT and NMR spectroscopy: The case of nivariol

Chemistry - A European Journal

Volumn 19, Issue 26, 2013, Pages 8525-8532

  Cen Pacheco, Francisco ^a,c   Rodríguez, Jaime ^b   Norte, Manuel ^a   Fernández, José J ^a   Hernández Daranas, Antonio ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b UNIVERSITY OF A CORUÑA   (Spain)

^c UNIVERSIDAD VERACRUZANA   (Mexico)

Author keywords

cluster compounds; conformational analysis; density functional calculations; natural products; NMR spectroscopy

Indexed keywords

CLUSTER COMPOUNDS; CONFORMATIONAL ANALYSIS; MOLECULAR CONFORMATION; NATURAL PRODUCTS; NMR CHEMICAL SHIFTS; SMALL ORGANIC MOLECULES; STRUCTURAL DETERMINATION; STRUCTURAL EVIDENCE;

CARBON; CHEMICAL SHIFT; CONFORMATIONS; DENSITY FUNCTIONAL THEORY; ETHERS; MOLECULES; STEREOCHEMISTRY;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

BIOLOGICAL PRODUCT; ETHER DERIVATIVE; FURAN DERIVATIVE; NIVARIOL;

ARTICLE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

BIOLOGICAL PRODUCTS; ETHERS; ETHERS, CYCLIC; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84879150619     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204272     Document Type: Article

References (41)

1. N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, K. Tachibana, J. Org. Chem. 1999, 64, 866-876.
2. G. Barone, L. Gomez-Paloma, D. Duca, A. Silvestri, R. Riccio, G. Bifulco, Chem. Eur. J. 2002, 8, 3233-3239.
3. G. Barone, D. Duca, A. Silvestri, L. Gomez-Paloma, R. Riccio, G. Bifulco, Chem. Eur. J. 2002, 8, 3240-3245.
4. G. Bifulco, P. Dambruoso, L. Gomez-Paloma, R. Riccio, Chem. Rev. 2007, 107, 3744-3779.
5. D. Menche, Nat. Prod. Rep. 2008, 25, 905-918.
6. D. Janssen, D. Albert, R. Jansen, R. Müller, M. Kalesse, Angew. Chem. 2007, 119, 4985-4988
7. Angew. Chem. Int. Ed. 2007, 46, 4898-4901.
8. N. Horstmann, D. Menche, Chem. Commun. 2008, 5173-5175.
9. M. Bock, K. Buntin, R. Müller, A. Kirschning, Angew. Chem. 2008, 120, 2341-2344
10. Angew. Chem. Int. Ed. 2008, 47, 2308-2311.
11. C. P. Butts, C. R. Jones, J. N. Harvey, Chem. Commun. 2011, 47, 1193-1195.
12. C. Farès, J. Hassfeld, D. Menche, T. Carlomagno, Angew. Chem. 2008, 120, 3782-3786; Angew. Chem. Int. Ed. 2008, 47, 3722- 3726
13. Angew. Chem. Int. Ed. 2008, 47, 3722-3726.
14. H. Sun, U. M. Reinscheid, E. L. Whitson, E. J. d'Auvergne, C. M. Ireland, A. Navarro-Vazquez, C. Griesinger, J. Am. Chem. Soc. 2011, 133, 14629-14636.
15. M. W. Lodewyk, M. R. Siebert, D. J. Tantillo, Chem. Rev. 2012, 112, 1839-1862.
16. S. G. Smith, J. M. Goodman, J. Am. Chem. Soc. 2010, 132, 12946-12959.
17. B. S. Dyson, J. W. Burton, T. Sohn, B. Kim, H. Bae, D. Kim, J. Am. Chem. Soc. 2012, 134, 11781-11790.
18. H. Seike, I. Ghosh, Y. Kishi, Org. Lett. 2006, 8, 3861-3864.
19. F. Khachik, A. Steck, U. A. Niggli, H. Pfander, J. Agric. Food Chem. 1998, 46, 4874-4884.
20. J. Napolitano, J. Gavín, C. García, M. Norte, J. J. Fernández, A. Hernández Daranas, Chem. Eur. J. 2011, 17, 6338-6347.
21. A. Meissner, O. W. Soerensen, Mag. Res. Chem. 2001, 39, 49-52.
22. P. Cuniasse, I. Raynal, A. Yiotakis, V. Dive, J. Am. Chem. Soc. 1997, 119, 5239-5248.
23. I. Paterson, S. M. Dalby, J. C. Roberts, G. J. Naylor, E. A. Guzmn, R. Isbrucker, T. P. Pitts, P. Linley, D. Divlianska, J. K. Reed, A. E. Wright, Angew. Chem. 2011, 123, 3277-3281
24. Angew. Chem. Int. Ed. 2011, 50, 3219-3223.
25. T. Caserta, V. Piccialli, L. Gomez-Paloma, G. Bifulco, Tetrahedron 2005, 61, 927-939.
26. Y. Morimoto, Org. Biomol. Chem. 2008, 6, 1709-1719.
27. Y. Morimoto, Y. Yata, Y. Nishikawa, Angew. Chem. 2007, 119, 6601-6604
28. Angew. Chem. Int. Ed. 2007, 46, 6481-6484.
29. G. Saielli, K. C. Nicolaou, A. Ortiz, H. Zhang, A. Bagno, J. Am. Chem. Soc. 2011, 133, 6072-6077.
30. J. W. Blunt, M. P. Hartshorn, T. J. McLennan, M. H. Munro, W. T. Robinson, S. C. Yorke, Tetrahedron Lett. 1978, 19, 69-72.
31. S. Sakemi, T. Higa, Tetrahedron Lett. 1986, 27, 4287-4290.
32. M. Hashimoto, T. Kan, K. Nozaki, M. Yanagiya, H. Shirahama, T. Matsumoto, Tetrahedron Lett. 1986, 27, 2885-2888.
33. J. J. Fernández, M. L. Souto, M. Norte, Nat. Prod. Rep. 2000, 17, 235-246.
34. A. R. B. Ola, A. M. Babey, C. Motti, B. F. Bowden, Aust. J. Chem. 2010, 63, 907-914.
35. T. Suzuki, M. Suzuki, A. Furusaki, T. Matsumoto, A. Kato, Y. Imanaka, E. Kurosawa, Tetrahedron Lett. 1985, 26, 1329-1332.
36. F. Cen-Pacheco, J. Villa-Pulgarin, F. Mollinedo, M. Norte, J. J. Fernandez, A. Hernandez Daranas, Mar. Drugs 2011, 9, 2220-2235.
37. F. Cen-Pacheco, F. Mollinedo, J. Villa-Pulgarin, M. Norte, J. J. Fernández, A. Hernández Daranas, Tetrahedron 2012, 68, 7275-7279.
38. H. Kigoshi, M. Ojika, Y. Shizuri, H. Niwa, K. Yamada, Tetrahedron Lett. 1982, 23, 5413-5414.
39. M. L. Souto, C. P. Manríquez, M. Norte, F. Leira, J. J. Fernández, Bioorg. Med. Chem. Lett. 2003, 13, 1261-1264.
40. F. Cen-Pacheco, J. Villa-Pulgarin, F. Mollinedo, M. Norte, A. Hernández Daranas, J. J. Fernández, Eur. J. Med. Chem. 2011, 46, 3302-3308.
41. Gaussian 09, Revision A.1, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.