Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg-Bäcklund reaction

Canadian Journal of Chemistry

Volumn 82, Issue 5, 2004, Pages 622-630

  Li, Yang ^a   Zhang, Yu ^a   Huang, Zhi ^a   Cao, Xiaoping ^a   Gao, Kun ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Ramberg B cklund reaction; Synthesis; Unsaturated amide alkaloids

Indexed keywords

ALCOHOLS; OXIDATION; PHASE TRANSITIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALKALOIDS; DICHLOROMETHANE (DCM);

NITROGEN COMPOUNDS;

ALCOHOL; ALKALOID DERIVATIVE; AMIDE; CHLOROACETAMIDE; DICHLOROMETHANE; POTASSIUM HYDROXIDE; SULFIDE; SULFONE;

ALKYLATION; ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; MITSUNOBU REACTION; OXIDATION;

EID: 3042841336     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v04-028     Document Type: Article

References (53)

1. (a) F. Kiuchi, N. Nakamura, Y. Tsuda, K. Kondo, and H. Yoshimura. Chem. Pharm. Bull. 36, 2452 (1988);
2. (b) H. Achenbach, W. Fietz, J. Wörth, R. Waibel, and J. Portecop. Planta Med. 52, 12 (1986);
3. (c) J.X. Araujo, E.V.L. Da-Cunha, M.C.O. Chaves, and A.I. Gray. Phytochemistry, 44, 559 (1997);
4. (d) B.G. Pring. J. Chem. Soc. Perkin Trans. 1, 1493 (1982);
5. (e) Q.L. Wu, Y.X. Feng, and J.S. Yang. Chin. Chem. Lett. 5, 203 (1994);
6. (f) Z.H. Ding, J.K. Ding, Z.L. Chen, P.Y. Bai, H. Nanao, and K. Hisashi. Phytochemistry, 30, 3797 (1991);
7. (g) F. Bohlmann, C. Zdero, and A. Suwita. Chem. Ber. 107, 1038 (1974);
8. (h) K. Likhitwitayawuid, N. Ruangrungsi, G.L. Lange, and C.P. Decicco. Tetrahedron, 43, 3689 (1987);
9. (i) B. Saadali, D. Boriky, M. Blaghen, M. Vanhaelen, and M. Talbi. Phytochemistry, 58, 1083 (2001);
10. (j) V.S. Parmar, S.C. Jain, K.S. Bisht, R. Jain, P. Taneja, A. Jha, O.D. Tyagi, A.K. Prasad, J. Wengel, C.E. Olsen, and P.M. Boll. Phytochemistry, 46, 597 (1997).
11. (a) H. Weenen, M.H.H. Nkunya, D.H. Bray, L.B. Mwasumbi, L.S. Kinabo, V.A.E.B. Kilimali, and J.B.P.A. Wijnberg. Planta Med. 56, 371 (1990);
12. (b) M.D.N. Hosana, C.A. Alberto, J.K. Massuo, S.B. Vanderlan, C.M.Y. Maria, J.C. Alberto, and F. Maysa. Phytochemistry, 55, 621 (2000);
13. (c) S. Bajad, K.L. Bedi, A.K. Singla, and R.K. Johri. Planta Med. 67, 176 (2001);
14. (d) S. Tsukamoto, B.C. Cha, and T. Ohta. Tetrahedron, 58, 1667 (2002).
15. (a) S.S. Bari, M.A. Sattar, R. Vig, A. Kumar, and N. Vasisht. J. Indian Chem. Soc. 67, 995 (1990);
16. (b) G.L. Kad, A.K. Arora, S. Singh, and J. Singh. Coll. Czech. Chem. Commun. 60, 1050 (1995);
17. (c) J.X. Araújo, C.M. Duarte, M.C.O. Chaves, J.P. Parente, C.A.M. Fraga, and E.J. Barreiro. Synth. Commun. 31, 117 (2001), and refs. therein;
18. (d) R. Schobert, S. Siegfried, and G.J. Gordon, J. Chem. Soc. Perkin Trans. 1, 2393 (2001);
19. (e) W.S. Lin, H.M. Wang, and L.C. Chen. J. Chin. Chem. Soc. (Taipei), 45, 159 (1998); 46, 963 (1999);
20. (e) W.S. Lin, H.M. Wang, and L.C. Chen. J. Chin. Chem. Soc. (Taipei), 45, 159 (1998); 46, 963 (1999);
21. (f) M. Abarbri, J.L. Parrain, and A. Duchêne. Synth. Commun. 28, 239 (1998), and refs. therein;
22. (g) T. Jeffery. Synth. Commun. 18, 77 (1988);
23. (h) B.M. Trost, M. Lautens, and B. Peterson. Tetrahedron Lett. 24, 4525 (1983);
24. (i) G.M. Strunz and H.J. Finlay. Can. J. Chem. 74, 419 (1996);
25. (j) S. Chandrasekhar, M.V. Reddy, K.S. Reddy, and C. Ramaro. Tetrahedron Lett. 41, 2667 (2000).
26. (a) F. Bohlmann and C. Hühn. Chem. Ber. 110, 1183 (1977);
27. (b) E.V. Dehmlow and A.R. Shamout. J. Chem. Res. Synop. 106 (1981);
28. (c) J.E. Semple. Org. Prep. Proced. Int. 27, 582 (1995);
29. (d) R. Bloch and D. Hassan-Gonzales. Tetrahedron, 42, 4975 (1986);
30. (e) T. Mandai, T. Moriyama, K. Tsujimoto, M. Kawada, and J. Otera. Tetrahedron Lett. 27, 603 (1986);
31. (f) N.A. Plobeck and J.E. Bäckvall. J. Org. Chem. 56, 4508 (1991);
32. (g) D.W. Ma and X.Y. Lu. Tetrahedron, 46, 3189 (1990);
33. (h) L. Crombie and M.A. Horsham. Tetrahedron Lett. 28, 4879 (1987), and refs. therein;
34. (i) R. Rossi, A. Carpita, and V. Lippolis. Synth. Commun. 21, 333 (1991);
35. (j) F. Babudri, V. Fiandanese, F. Naso, and A. Punzi. Tetrahedron Lett. 35, 2067 (1994);
36. (k) M.C. Bernabeu, R. Chinchilla, and C. Nájera. Tetrahedron Lett. 36, 3901 (1995).
37. (a) T.L. Chan, S. Fong, Y. Li, T.O. Man, and C.D. Poon. J. Chem. Soc. Chem. Commun. 1771 (1994);
38. (b) X.P. Cao, T.L. Chan, H.F. Chow, and J. Tu. J. Chem. Soc. Chem. Commun. 1297 (1995);
39. (c) X.P. Cao, T.L. Chan, and H.F. Chow. Tetrahedron Lett. 37, 1049 (1996);
40. (d) X.P. Cao. Tetrahedron, 58, 1301 (2002);
41. (e) X.P. Cao, Y.Y. Yang, and X.L. Wang. J. Chem. Soc. Perkin Trans. 1, 2485 (2002).
42. (a) C.Y Meyers, A.M. Malte, and W.S. Matthews. J. Am. Chem. Soc. 91, 7510 (1969);
43. (b) J.M. Clough. In Comprehensive organic synthesis. Edited by B.M. Trost and I. Fleming. Pergamon Press, Oxford. 1991. p. 861;
44. (c) G. Casy and R.J.K. Taylor. Org. React. 62, 357 (2003)
45. H. Seguin, D. Gardette, M.F. Moreau, J.C. Madelmont, and J.C. Gramain. Synth. Commun. 28, 4257 (1998).
46. O. Mitsunobu. Synthesis, 1 (1981).
47. B.M. Trost and D.P. Curran. Tetrahedron Lett. 22, 1287 (1981).
48. (a) W.A. Donaldson, M.J. Jin, and P.T. Bell. Organometallics, 12, 1174 (1993);
49. (b) G. Maiti, S. Adhikari, and S.C. Roy. Tetrahedron Lett. 35, 3985 (1994);
50. (c) C. Bonini, C. Federici, L. Rossi, and G. Righi. J. Org. Chem. 60, 4803 (1995).
51. (a) E. Juaristi and J.S. Cruz-Sánchez. J. Org. Chem. 53, 3334 (1988).
52. (b) K.N. Gurudutt, S. Rao, P. Srinivas, and S. Srinivas. Tetrahedron, 51, 3045 (1995).
53. O. Hofer, H. Greger, W. Robien, and A. Werner. Tetrahedron, 42, 2707 (1986).