IR, VCD, 1H and 13C NMR experimental and theoretical studies of a natural guaianolide: Unambiguous determination of its absolute configuration

Journal of Molecular Structure

Volumn 791, Issue 1-3, 2006, Pages 186-192

  Bercion, Sylvie ^a   Buffeteau, Thierry ^b   Lespade, Laure ^b   Martin, Marie Anna Couppe deK ^a  

^a EA 3639   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Absolute configuration; DFT calculation; Guaianolide; NMR; Sesquiterpenoids; VCD

Indexed keywords

INFRARED RADIATION; ISOMERS; NUCLEAR MAGNETIC RESONANCE; PROBABILITY DENSITY FUNCTION; SPECTRUM ANALYZERS; VIBRATIONS (MECHANICAL);

ABSOLUTE CONFIGURATION; GUAIANOLIDE; SESQUITERPENOIDS;

AROMATIC COMPOUNDS;

HEDYOSMUM ARBORESCENS;

EID: 33746905172     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2006.01.030     Document Type: Article

References (30)

1. Connolly J.D., and Hill R.A. Dictionary of Terpenoids, Mono- and Sesquiterpenoids vol. 1 (1991), Chapman & Hall, London p. 514
2. Rodriguez E., Towers G.H.N., and Mitchell C. Phytochemistry 15 (1976) 1573
3. Tukov F.F., Anand S., Gadepalli R.S.V.S., Gunatilaka A.A.L., Matthews J.C., and Rimoldi J.M. Chem. Res. Toxicol. 17 (2004) 1170-1176
4. Taniguchi M., Kataoka T., et al. Biosci. Biotechnol. Biochem. 59 (1995) 2064
5. Yuuya S., Hagiwara H., Suzuki T., Ando M., Yamada A., Suda K., Kataoka T., and Nagai K. J. Nat. Prod. 62 (1999) 22
6. Kupchan S.M., Giacobbe T.J., Krull I.S., Thomas S.M., Eakin M.A., and Fessler D.C. J. Org. Chem. 35 (1970) 3539
7. Bercion S., Couppe de K/Martin M.-A., Baltaze J.-P., and Bourgeois P. Fitoterapia 76 (2005) 620-624
8. Blay G., Bargues V., Cardona L., and Garcia B. J. Pedro J. Org. Chem. 65 (2000) 6703
9. Nafie L.A., Dukor R.K., and Freedman T.B. In: Chalmers J.M., and Griffiths P.R. (Eds). Handbook of Vibrational Spectroscopy vol. 1 (2002), Wiley, Chichester 731-744
10. Freedman T.B., Cao X., Dukor R.K., and Nafie L.A. Chirality 15 (2003) 743-758 (and references therein)
11. Stephens P., and Delvin F.J. Chirality 12 (2000) 172-179
12. Buffeteau T., Lagugné-Labartet F., and Sourisseau C. Appl. Spectrosc. 59 (2005) 732-745
13. Nafie L.A., and Vidrine D.W. In: Ferraro J.R., and Basile L.J. (Eds). Fourier Transform Infrared Spectroscopy vol. 3 (1982), Academic Press, New York 83
14. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nagajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick,A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Allaham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, gaussian 03, Gaussian, Inc., Pittsburgh, PA, 2003.
15. London F. J. Phys. Radium, Paris 8 (1937) 397
16. Mc Weeny R. Phys. Rev. 126 (1962) 1028
17. Ditchfield R. Mol. Phys. 27 (1974) 789
18. Dodds J.L., McWeeny R., and Sadlej A.J. Mol. Phys. 41 (1980) 1419
19. Wolinski K., Hilton J.F., and Pulay P. J. Am. Chem. Soc. 112 (1990) 8251
20. Cheesman J.R., Frisch M.J., Delvin F.J., and Stephens P.J. Chem. Phys. Lett. 252 (1996) 211-220
21. Becke A.D. J. Chem. Phys. 98 (1993) 5648
22. Becke A.D. J. Chem. Phys. 107 (1997) 8554
23. Lee C., Yang W., and Parr G.R. Phys. Rev. B 37 (1988) 785
24. Mehlich B., Savin A., Stoll H., and Preum H. Chem. Phys. Lett. 157 (1989) 200
25. Hehre W.J., Random L., Schleyer P.V.R., and Pople J.A. Ab initio Molecular Orbital Theory (1986), Wiley, New York
26. Galasso V., Asaro F., Berti F., Kovač B., Habuš I., and De Risi C. Chem. Phys. 301 (2004) 33
27. Gonçalves N.S., Cristiano R., Pizzolatti M.G., and da Silva Miranda F. J. Mol. Struct. 733 (2005) 53-61
28. V. Enchev, N. Markova, S. Angelova, J. Phys. Chem. A 109 (2005) 8904.
29. Pulay P.J. Comput. Chem. 3 (1982) 556
30. He J., and Polavarapu P.L. Spectrochim. Acta Part A 61 (2005) 1327