114. A reinvestigation of the oxidative rearrangement of yohimbane-type alkaloids: Part B. Formation of oxindol (=1,3-dihydro-2H-indol-2-one) derivatives

Helvetica Chimica Acta

Volumn 79, Issue 5, 1996, Pages 1361-1378

  Stahl, Reto ^a   Borschberg, Hans Jürg ^a   Acklin, Pierre ^b  

^a ETH ZURICH   (Switzerland)

^b CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; YOHIMBAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; THEORY; THERMODYNAMICS;

EID: 0030017772     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19960790510     Document Type: Article

References (43)

1. R. Stahl, H.-J. Borschberg, Helv. Chim. Acta 1994, 77, 1331.
2. J. S. Bindra, 'Oxindole Alkaloids', in 'The Alkaloids', Ed R. H. F Manske, Academic Press, New York, 1973, Vol. XIV, pp. 83-121, R. T. Brown, in 'The Monoterpenoid Indole Alkaloids', Ed. J. E. Saxton, John Wiley & Sons, New York, 1983, Chapt. III, pp. 85-96; J. E. Saxton, 'Alkaloids of Mitragyna and Ourouparia Species', in 'The Alkaloids', Ed. R. H. F. Manske, Academic Press, New York, 1965, Vol. VIII, pp. 59-91; J. E. Saxton, ibid., 1968, Vol. X, pp. 521-548, M. Ikeda, Y. Tamura, Heterocycles 1980, 6, 867.
3. J. S. Bindra, 'Oxindole Alkaloids', in 'The Alkaloids', Ed R. H. F Manske, Academic Press, New York, 1973, Vol. XIV, pp. 83-121, R. T. Brown, in 'The Monoterpenoid Indole Alkaloids', Ed. J. E. Saxton, John Wiley & Sons, New York, 1983, Chapt. III, pp. 85-96; J. E. Saxton, 'Alkaloids of Mitragyna and Ourouparia Species', in 'The Alkaloids', Ed. R. H. F. Manske, Academic Press, New York, 1965, Vol. VIII, pp. 59-91; J. E. Saxton, ibid., 1968, Vol. X, pp. 521-548, M. Ikeda, Y. Tamura, Heterocycles 1980, 6, 867.
4. J. S. Bindra, 'Oxindole Alkaloids', in 'The Alkaloids', Ed R. H. F Manske, Academic Press, New York, 1973, Vol. XIV, pp. 83-121, R. T. Brown, in 'The Monoterpenoid Indole Alkaloids', Ed. J. E. Saxton, John Wiley & Sons, New York, 1983, Chapt. III, pp. 85-96; J. E. Saxton, 'Alkaloids of Mitragyna and Ourouparia Species', in 'The Alkaloids', Ed. R. H. F. Manske, Academic Press, New York, 1965, Vol. VIII, pp. 59-91; J. E. Saxton, ibid., 1968, Vol. X, pp. 521-548, M. Ikeda, Y. Tamura, Heterocycles 1980, 6, 867.
5. J. S. Bindra, 'Oxindole Alkaloids', in 'The Alkaloids', Ed R. H. F Manske, Academic Press, New York, 1973, Vol. XIV, pp. 83-121, R. T. Brown, in 'The Monoterpenoid Indole Alkaloids', Ed. J. E. Saxton, John Wiley & Sons, New York, 1983, Chapt. III, pp. 85-96; J. E. Saxton, 'Alkaloids of Mitragyna and Ourouparia Species', in 'The Alkaloids', Ed. R. H. F. Manske, Academic Press, New York, 1965, Vol. VIII, pp. 59-91; J. E. Saxton, ibid., 1968, Vol. X, pp. 521-548, M. Ikeda, Y. Tamura, Heterocycles 1980, 6, 867.
6. J. S. Bindra, 'Oxindole Alkaloids', in 'The Alkaloids', Ed R. H. F Manske, Academic Press, New York, 1973, Vol. XIV, pp. 83-121, R. T. Brown, in 'The Monoterpenoid Indole Alkaloids', Ed. J. E. Saxton, John Wiley & Sons, New York, 1983, Chapt. III, pp. 85-96; J. E. Saxton, 'Alkaloids of Mitragyna and Ourouparia Species', in 'The Alkaloids', Ed. R. H. F. Manske, Academic Press, New York, 1965, Vol. VIII, pp. 59-91; J. E. Saxton, ibid., 1968, Vol. X, pp. 521-548, M. Ikeda, Y. Tamura, Heterocycles 1980, 6, 867.
7. W. O. Godtfredsen, S. Vangedal, Acta Chim. Scand. 1956, 10, 1414.
8. J. E. Saxton, 'The Alkaloids', Ed R. H. F. Manske, Academic Press, New York, 1964, Vol. VII, p 90.
9. N. Finch, W. I. Taylor, J. Am. Chem. Soc. 1962, 84, 1318; ibid. p. 3871.
10. N. Finch, W. I. Taylor, J. Am. Chem. Soc. 1962, 84, 1318; ibid. p. 3871.
11. J. Shavel, Jr., H. Zinnes, J. Am. Chem. Soc. 1962, 84, 1320; H. Zinnes, J. Shavel, Jr , J. Org. Chem. 1966, 31, 1765
12. J. Shavel, Jr., H. Zinnes, J. Am. Chem. Soc. 1962, 84, 1320; H. Zinnes, J. Shavel, Jr , J. Org. Chem. 1966, 31, 1765
13. D. V. C. Awang, A. Vincent, D. Kindack, Can. J. Chem. 1984, 62, 2667
14. R. Güller, H.-J. Borschberg, Helv Chim. Acta 1993, 76, 1647.
15. N. Finch, C. W. Gemenden, I. H.-C. Hsu, A. Kerr, G. A. Sim, W. I. Taylor, J. Am Chem. Soc. 1965, 87, 2229.
16. E. Wenkert, C.-J. Chang, H. P. S. Chawla, D. W. Cochran, E. W. Hagaman, J. C. King, K. Orito, J. Am. Chem. Soc. 1976, 98, 3645.
17. D. Herlem, F. Khuong-Huu, Tetrahedron 1979, 35, 633.
18. F. Bohlmann, Chem. Ber. 1958, 91, 2157.
19. L. J. Dolby, G W. Gribble, J. Org. Chem. 1967, 32, 1391.
20. R. P. Borris, A. Guggisberg, M. Hesse, Helv. Chim. Acta 1984, 67, 455.
21. D. S. Nunes, L. Koike, J J. Taveira, F. de A. M. Reis, Phytochemistry 1992, 31, 2507.
22. J.-Y. Laronze, J. Laronze, D. Royer, J. Lévy, J. Le Men, Bull. Soc. Chim. Fr. 1977, 1215
23. H. Kondo, T. Fukuda, M. Tomita, J. Pharm. Soc. Jpn. 1928, 48, 54; T. Nozoye, Pharm. Bull. (Jpn.) 1958, 6, 300; J. C. Seaton, M. D. Nair, O. E. Edwards, L. Marion, Can. J. Chem. 1960, 38, 1035.
24. H. Kondo, T. Fukuda, M. Tomita, J. Pharm. Soc. Jpn. 1928, 48, 54; T. Nozoye, Pharm. Bull. (Jpn.) 1958, 6, 300; J. C. Seaton, M. D. Nair, O. E. Edwards, L. Marion, Can. J. Chem. 1960, 38, 1035.
25. H. Kondo, T. Fukuda, M. Tomita, J. Pharm. Soc. Jpn. 1928, 48, 54; T. Nozoye, Pharm. Bull. (Jpn.) 1958, 6, 300; J. C. Seaton, M. D. Nair, O. E. Edwards, L. Marion, Can. J. Chem. 1960, 38, 1035.
26. E. Wenkert, J. H. Udelhofen, N. K. Bhattacharyya, J. Am. Chem. Soc. 1959, 81, 3763.
27. G. Hahn, E. Kappes, H. Ludewig, Chem. Ber 1934, 67, 686; R. Majima, S. Murahashi, Proc. Imp. Acad. (Tokyo) 1934, 70, 341
28. G. Hahn, E. Kappes, H. Ludewig, Chem. Ber 1934, 67, 686; R. Majima, S. Murahashi, Proc. Imp. Acad. (Tokyo) 1934, 70, 341
29. M.-M. Janot, R Goutarel, A Le Hir, M. Amin, V. Prelog, Bull. Soc. Chim Fr. 1952, 1085.
30. P. Deslongchamps, 'Stereoelectronic Effects in Organic Chemistry', Pergamon Press, Oxford, 1983, Chapt. 6.
31. C. Pellegrini, C. Strässler, M. Weber, H.-J. Borschberg, Tetrahedron: Asymmetry 1994, 5, 1979; C. Pellegrini, M. Weber, H.-J. Borschberg, Helv. Chim. Acta 1996, 79, 151.
32. C. Pellegrini, C. Strässler, M. Weber, H.-J. Borschberg, Tetrahedron: Asymmetry 1994, 5, 1979; C. Pellegrini, M. Weber, H.-J. Borschberg, Helv. Chim. Acta 1996, 79, 151.
33. S. A. Boyd, W. J. Thompson, J. Org. Chem. 1987, 52, 1790; M. Nakagawa, H. Fukushima, T. Kawate, M. Hongu, T. Une, S.-i. Kodato, M. Taniguchi, T. Hino, Chem. Pharm. Bull. 1989, 37, 23; H. Irikawa, S. Mutoh, M. Uehara, Y. Okimura, Bull. Chem. Soc. Jpn. 1989, 62, 3031.
34. S. A. Boyd, W. J. Thompson, J. Org. Chem. 1987, 52, 1790; M. Nakagawa, H. Fukushima, T. Kawate, M. Hongu, T. Une, S.-i. Kodato, M. Taniguchi, T. Hino, Chem. Pharm. Bull. 1989, 37, 23; H. Irikawa, S. Mutoh, M. Uehara, Y. Okimura, Bull. Chem. Soc. Jpn. 1989, 62, 3031.
35. S. A. Boyd, W. J. Thompson, J. Org. Chem. 1987, 52, 1790; M. Nakagawa, H. Fukushima, T. Kawate, M. Hongu, T. Une, S.-i. Kodato, M. Taniguchi, T. Hino, Chem. Pharm. Bull. 1989, 37, 23; H. Irikawa, S. Mutoh, M. Uehara, Y. Okimura, Bull. Chem. Soc. Jpn. 1989, 62, 3031.
36. E. Wenkert, D. K. Roychaudhuri, J. Am. Chem. Soc. 1958, 80, 1613, and ref. cit therein.
37. E. Wenkert, D. K. Roychaudhuri, J. Org. Chem. 1956, 21, 1315.
38. S. J. Weiner, P. A. Kollmann, D. Case, U. C. Singh, C. Alagona, S. Profeta, P. Weiner, J. Am. Chem. Soc. 1984, 106, 765.
39. J M. Goodman, W. C. Still, J. Comput. Chem. 1991, 12, 1110.
40. J. Ponder, F. M. Richards, J. Comput. Chem. 1987, 8, 1016.
41. W. C. Still, A. Tempczyk, R. C. Hawley, T. Hendrickson, J Am. Chem. Soc. 1990, 112, 6127.
42. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902.
43. J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209.