Detailed 1H and 13C NMR structural assignment and relative stereochemistry determination for three new and one known semi-synthetic sesquiterpene lactones

Journal of Molecular Structure

Volumn 1008, Issue , 2012, Pages 24-28

  Sass, Daiane Cristina ^a   Heleno, Vladimir Constantino Gomes ^b   Soares, Ana Carolina Ferreira ^b   Lopes, João Luis Callegari ^a   Constantino, Mauricio Gomes ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSIDADE DE FRANCA   (Brazil)

Author keywords

2D NMR; 13C NMR; 1H NMR; Furanoheliangolides; Sesquiterpene lactones

Indexed keywords

COUPLING CONSTANTS; FURANOHELIANGOLIDES; NMR ANALYSIS; SESQUITERPENE LACTONES; STRUCTURAL ASSIGNMENTS;

HYDROGEN;

STEREOCHEMISTRY;

EID: 84855440118     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2011.11.012     Document Type: Article

References (20)

1. P. Rüngeler, V. Castro, G. Mora, N. Gören, W. Vichnewski, H.L. Pahl, I. Merfort, and T.J. Schmidt Bioorg. Med. Chem. 7 1999 2343
2. D.S. Brown, and L.A. Paquette J. Org. Chem. 57 1992 4512
3. P.G. McDougal, Y. Oh, and D. VanDerveer J. Org. Chem. 54 1989 91
4. W. Vichnewski, A.M. Takahashi, A.M.T. Nasi, D.C.R.G. Gonalves, D.A. Dias, J.N.C. Lopes, V.L. Goedken, A.B. Gutiérrez, and W. Herz Phytochemistry 28 1989 1441
5. F. Bohmann, C. Zdero, H. Robinson, and R.M. King Phytochemistry 21 1982 685
6. W.R. Cunha, J.L.C. Lopes, W. Vichnewski, J.G. Díaz, and W. Herz Phytochemistry 39 1995 387
7. M.L.C. Borsato, C.F.F. Grael, G.E.P. Souza, and N.P. Lopes Phytochemistry 55 2000 809
8. O.G. Miguel, E.O. Lima, V.M.F. Morais, S.T.A. Gomes, F. Dellemorado, A.B. Cruz, R.C.B. Cruz, and V. Cechinel Phytother. Res. 13 1996 694
9. T.J. Schmidt Curr. Org. Chem. 3 1999 577
10. V.C.G. Heleno, K.T. De Oliveira, J.L.C. Lopes, N.P. Lopes, and A.G. Ferreira Magn. Reson. Chem. 46 2008 576
11. V.C.G. Heleno, A.E.M. Crotti, M.G. Constantino, N.P. Lopes, and J.L.C. Lopes Magn. Reson. Chem. 42 2004 364
12. K.S.P. Perry, E. Miguez, M.B. De Amorim, M.A.D. Boaventura, and A.J.R. Da Silva Magn. Reson. Chem. 39 2001 219
13. A. Ulubelen, N. Gören, T.Y. Jiang, L. Scott, M. Tianasoa-Ramomojy, and J.K. Snyder Magn. Reson. Chem. 33 1995 900
14. D.C. Sass, V.C.G. Heleno, J.L.C. Lopes, and M.G. Constantino Tetrahedron Lett. 49 2008 3877
15. D.C. Sass, V.C.G. Heleno, G.O. Morais, J.L.C. Lopes, N.P. Lopes, M.G. Constantino, Org. Biomol. Chem. (2011) doi: 10.1039/c1ob05734k.
16. P. Chiu, Z. Li, and K.C.M. Fung Tetrahedron Lett. 44 2003 455
17. T.M. Koenig, J.F. Daeuble, D.M. Brestensky, and J.M. Stryker Tetrahedron Lett. 31 1990 3237
18. W.S. Mahoney, D.M. Brestensky, and J.M. Stryker J. Am. Chem. Soc. 110 1988 291
19. W.K. Chung, and P. Chiu Synlett 55 2005
20. B.H. Lipshutz, W. Chrisman, K. Noson, P. Papa, J.A. Scalfani, R.W. Vivian, and J.M. Keith Tetrahedron 56 2000 2779