Molecular rearrangement of epoxide derived from sesquiterpenes by Lewis acid catalysis

Tetrahedron Asymmetry

Volumn 21, Issue 9-10, 2010, Pages 1272-1277

  Haib, Abderrahim El ^a,b,c   Benharref, Ahmed ^c   Parrs Maynadié, Sandra ^a,b   Manoury, Eric ^a,b   Daran, Jean Claude ^a,b   Urrutigoïty, Martine ^a,b   Gouygou, Maryse ^a,b  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^b UNIVERSITÉ DE TOULOUSE   (France)

^c FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

(3,10,10) TRIMETHYLTRICYCLO[5.4.4]DODEC 4 ENE 2 OL; 1,5,8,8 TETRAMETHYLBICYCLO[5.4.0]UNDECAN 2 ONE; 3,11,11 TRIMETHYLTRICYCLO[5.4.1 (3,7).0]DODECAN 2 ONE; BORON TRIFLUORIDE ETHERATE; EPOXIDE; ETHER DERIVATIVE; KETONE; LEWIS ACID; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELIMINATION REACTION; ENANTIOMER; HYDROGEN BOND; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 77956683171     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.04.024     Document Type: Article

References (52)

1. A. Pfau, and P.L. Plattner Helv. Chim. Acta 17 1934 129
2. G.S. Krishna Rao, S. Dev, and P.C. Guha J. Indian Chem. Soc. 29 1952 721
3. J.B. Berdenberg, and H. Erdtmann Acta Chem. Scand. 15 1961 685
4. M. Plattier, and P. Teisseire Recherches 19 1974 131
5. T.C. Joseph, and S. Dev Tetrahedron 24 1968 3809
6. T.C. Joseph, and S. Dev Tetrahedron 24 1968 3841
7. T.C. Joseph, and S. Dev Tetrahedron 24 1968 3853
8. S.C. Bisary, and S. Dev Tetrahedron 24 1968 3869
9. R. Shankaranyan, S. Krishmappa, and S. Dev Tetrahedron 33 1977 885
10. M. Plattier, P. Rouiller, and P. Teisseire Recherches 19 1974 145
11. J. Daunis, R. Jacquier, H. Lopez, and Ph. Viallefont J. Chem. Res. 1981 639
12. A. Benharref, A. Bernardini, S. Fkih Tetouani, R. Jacquier, and Ph. Viallefont J. Chem. Res. 1981 4329
13. A. Benharref, A. Chekroun, and J.P. Lavergne Bull. Soc. Chim. Fr. 128 1991 738
14. A. Chiaroni, M. Pais, C. Riche, A. Benharref, A. Chekroun, and J.P. Lavergne Acta Crystallogr., Sect. C 47 1991 1945
15. A. Chiaroni, C. Riche, A. Benharref, A. Chekroun, and J.P. Lavergne Acta Crystallogr., Sect. C 48 1992 1720
16. A. Chiaroni, C. Riche, A. Benharref, H. El Jamili, and E. Lassaba Acta Crystallogr., Sect. C 51 1995 1171
17. A. Chiaroni, C. Riche, A. Benharref, E. Lassaba, and A. Baouid Acta Crystallogr., Sect. C 52 1996 2504
18. A. Chiaroni, C. Riche, E. Lassaba, and A. Benharref Acta Crystallogr., Sect. C 52 1996 3240
19. E. Lassaba, H. El Jamili, A. Chekroun, A. Benharref, A. Chiaroni, C. Riche, and J.P. Lavergne Synth. Commun. 28 1998 2641
20. E. Lassaba, A. Chekroun, A. Benharref, A. Chiaroni, C. Riche, and J.P. Lavergne Bull. Soc. Chim. Fr. 106 1997 281
21. E. Lassaba, H. El Jamili, A. Benharref, A. Chiaroni, C. Riche, and M. Pierrot Bull. Soc. Chim. Fr. 106 1997 773
22. A. Chekroun, A. Jarid, A. Benharref, and A. Boutalib J. Org. Chem. 65 2000 4431
23. A. Chekroun, A. Jarid, A. Benharref, and A. Boutalib J. Mol. Struct. (Theochem.) 588 2002 201
24. H.O. House J. Am. Chem. Soc. 77 1955 3070 3075
25. B. Rickborn, and R.M. Gerkin J. Am. Chem. Soc. 93 1971 1693
26. E.J. Corey, R.L. Danheiser, and S. Chandrasekaran J. Org. Chem. 41 1976 260
27. S. Kulasegaram, and R.J. Kulawiec J. Org. Chem. 62 1997 6547
28. B.C. Ranu, and U. Jana J. Org. Chem. 63 1998 8212
29. A.M. Anderson, J.M. Blazek, P. Garg, B.J. Payne, and R.S. Mohan Tetrahedron Lett. 41 2000 1527
30. K.A. Bhatia, K.J. Eash, N.M. Leonard, M.C. Oswald, and R.S. Mohan Tetrahedron Lett. 42 2001 8129
31. C.M. Marson, C.A. Oare, J. McGregor, T. Walsgrove, T.J. Grinter, and H. Adams Tetrahedron Lett. 44 2003 141
32. K. Suda, T. Kikkawa, S. Nakajima, and T. Takanami J. Am. Chem. Soc. 126 2004 9554
33. M.W.C. Robinson, K.S. Pilinger, and A.E. Graham Tetrahedron Lett. 47 2006 5919
34. P. Mathew, D. Mathew, and C.V. Asokan Synth. Commun. 37 2007 661
35. Y. Kita, S. Matsuda, R. Inoguchi, J.K. Ganesh, and H. Fujioka J. Org. Chem. 71 2006 5191
36. G. Islas-Gonzalez, J. Benet-Buchholz, M.A. Maestro, A. Riera, and M.A. Pericas J. Org. Chem. 71 2006 1537
37. T.J. Snape Chem. Soc. Rev. 36 2007 1823
38. I.V. Ilina, K.P. Volcho, V.A. Korchagina, V.A. Barkhash, and N.F. Salakhutdinov Russ. J. Org. Chem. 43 2007 56
39. D.J. Tantillo J. Phys. Org. Chem. 21 2008 561
40. B. Reif, M. Kôck, R. Kerssebaum, H. Kang, W. Fenical, and C. Griesinger J. Magn. Reson., Ser A 118 1996 282
41. A.L. Spek J. Appl. Crystallogr. 36 2003 7
42. M.C. Etter, J.C. MacDonald, and J. Bernstein Acta Crystallogr., Sect. B 46 1990 256
43. J. Bernstein, R.E. Davis, L. Shimoni, and N.-L. Chang Angew. Chem., Int. Ed. Engl. 34 1995 1555
44. 1H NMR, IR and mass spectroscopy, see Liu, H.-J.; Browne, E. N. Can. J. Chem., 1987, 65, 182.
45. The minor compound 6 has already been obtained by dehydrogenation of the natural mixture of himachalenes from the essential oil of Atlas Cedar, see T.C. Joseph, and S. Dev Tetrahedron 24 1968 3829
46. B. Abouhamza, S. Allaoud, and A. Karim Molecules 6 2001 M236
47. At 589, 578, 546, 436 and 365 nm.
48. X.A. Dominguez, V.H. Sanchez, G.S. Garcia, B.G. Espinosa, H.J. Williams, C. Ortiz, A.I. Scott, and J.H. Reibenspies J. Nat. Prod. 55 1992 221
49. C.M. Houlilan, C.T. Ho, and S.S. Chang J. Am. Oil Chem. Soc. 61 1984 1036
50. A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, A. Guagliardi, A.G.G. Moliterni, G. Polidori, and R. Spagna J. Appl. Crystallogr. 32 1999 115
51. Sheldrick, G. M. shelxl97. Program for crystal structure refinement, University of Göttingen, Germany, 1997.
52. L.J. Farrugia J. Appl. Crystallogr. 30 1997