Application of the Mitsunobu reaction in the field of alkaloids

Journal of Heterocyclic Chemistry

Volumn 34, Issue 2, 1997, Pages 349-365

  Simon, Csaba ^a   Hosztafi, Sándor ^a   Makleit, Sandor ^b  

^a Alkaloida Chemical Company Ltd   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; UNINDEXED DRUG;

CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REVIEW; SYNTHESIS;

EID: 0030941221     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340201     Document Type: Review

References (86)

1. O. Mitsunobu, Synthesis, 1 (1981).
2. B. R. Castro, Org React., 29, 1 (1983).
3. D. L. Hughes, Org. React., 42, 335 (1992).
4. D. L. Hughes, Org. Prep. Proced. Int., 28, 127 (1996).
5. R. D. Guthrie and I. D. Jenkins, Aust. J. Chem., 35, 767 (1982).
6. E. Grochowski, B. D. Hilton, R. J. Kupper and C. J. Michejda, J. Am. Chem. Soc., 104, 6876 (1982).
7. M. von Itzstein and I. D. Jenkins, Aust. J. Chem., 35, 557 (1983).
8. W. Adam, N. Narita and Y. Nishizawa, J. Am. Chem. Soc., 106, 1843 (1984).
9. M. Varasi, K. A. M. Walker and M. Z. Maddox, J. Org. Chem., 52, 4235 (1987).
10. D. L. Hughes, R. A. Reamer, J. J. Bergan and E. J. J. Grabowski, J. Am. Chem. Soc., 110, 6487 (1988).
11. D. Crich, H. Dyker and R. J. Harris, J. Org. Chem., 54, 257 (1989).
12. A. Pautard-Cooper and S. A. Evans, J. Org. Chem., 54, 2485 (1989).
13. D. Camp and I. D. Jenkins, J. Org. Chem., 54, 3045 (1989).
14. D. Camp and I. D. Jenkins, J. Org. Chem., 54, 3049 (1989).
15. D. Camp and I. D. Jenkins, Aust. J. Chem., 45, 47 (1992).
16. S. R. Wilson, J. Perez and A. Pasternak, J. Am. Chem. Soc., 115, 1994 (1993).
17. D. Camp, G. R. Hanson and I. D. Jenkins, J. Org Chem., 60, 2977 (1995).
18. A. S. Amarasekara and A. Hassner, Tetrahedron Letters., 28, 3151 (1987).
19. K. Shishido, K. Tanaka, K. Fukumoto and T. Kametani, Tetrahedron Letters, 24, 2783 (1983).
20. K. Shishido, K. Tanaka, K. Fukumoto and T. Kametani, Chem. Pharm. Bull., 33, 532 (1985).
21. S. Takano and K. Shishido, Chem. Pharm. Bull., 32, 3892 (1984).
22. R. W. Hoffman and A. Endesfelder, Liebigs Ann. Chem., 1823 (1986).
23. I. H. Sanchez, F. J. Lopez, J. J. Soria, M. I. Larraza and H. J. Flores, J. Am. Chem. Soc., 105, 7640 (1983).
24. L. A. Paquette, D. Friedrich, E. Pinard, J. P. Williams, D. St. Laurent and B. A. Roden, J. Am. Chem. Soc., 115, 4377 (1993).
25. A. G. Schultz, M. A. Holoboski and M. S. Smyth, J. Am. Chem. Soc., 118, 6210 (1996).
26. K. Tomioka and K. Koga, Tetrahedron Letters, 21, 2321 (1980).
27. H. Takahata, Y. Banba and T. Momose, Tetrahedron; Asymmetry, 1, 763 (1990).
28. M. Zeches, T. Ravao, B. Richard, G. Massiot and L. Le Men-Olivier, Tetrahedron Letters, 25, 659 (1984).
29. G. Palmisano, B. Danieli, G. Lesma and R. Riva, J. Chem. Soc., Perkin Trans, 1, 923 (1985).
30. H. Ina and C. Kibayashi, Tetrahedron Letters, 32, 4147 (1991).
31. H. Ina and C. Kibayashi, J. Org. Chem., 58, 52 (1993).
32. E. Gössinger, Monatsh. Chem., 111, 143 (1980).
33. [33) E. Gössinger, Monatsh. Chem., 111, 783 (1980).
34. Cs. Simon, S. Hosztafi and S. Makleit, Synth. Commun., 21, 407 (1991).
35. S. Hosztafi, Cs. Simon and S. Makleit, Heterocycles, 36, 1509 (1993).
36. Cs. Simon, S. Hosztafi and S. Makleit, Tetrahedron, 50, 9757 (1994).
37. S. Hosztafi, I. Köhegyi, Cs. Simon and S. Fürst, Arzneim. Forsch., 43, 2100 (1993).
38. Cs. Simon, S. Hosztafi and S. Makleit, Magy. Kem. Foly., 98, 15 (1992).
39. R. Hohlbrugger and W. Klötzer, Chem. Ber., 112, 3486 (1979).
40. J. Reisch, A. A. W. Voerste, M. Top and P. Dziemba, Monatsh. Chem., 123, 473 (1992).
41. R. J. Heffner, J. Jiang and M. M. Joullie, J. Am. Chem. Soc., 114, 10181 (1992).
42. K. A. Parker and D. Fokas, J. Am. Chem. Soc., 114, 9688 (1992).
43. S. Takano, M. Akiyama and K. Ogasawara, J. Chem. Soc., Perkin Trans. 1, 2447 (1985).
44. J. Sisko, J. R. Henry and S. M. Weinreb, J. Org. Chem., 58, 4945 (1993).
45. H. Brunner, J. Bügler and B. Nuber, Tetrahedron; Asymmetry, 6, 1699 (1995).
46. M. G. Banwell, Pure Appl. Chem., 68, 539 (1996).
47. T. Yamane and K. Ogasawara, Synlett, 925 (1996).
48. J. A. Wendt and J. Aubé, Tetrahedron Letters, 37, 1531 (1996).
49. P. C. Heidt, S. C. Bergmeier and W. H. Pearson, Tetrahedron Letters, 31, 5441 (1990).
50. W. H. Pearson and Ko-C. Lin, Tetrahedron Letters, 31, 7571 (1990).
51. W. H. Pearson and S. C. Bergmeier, J. Org. Chem., 56, 1976 (1991).
52. W. H. Pearson, S. C. Bergmeier and J. P. Williams, J. Org. Chem., 57, 3977 (1992).
53. W. H. Pearson and E. J. Hembre, J. Org. Chem., 61, 5537 (1996).
54. W. H. Pearson and E. J. Hembre, J. Org. Chem., 61, 5546 (1996).
55. J. M. Schkeryantz and W. H. Pearson, Tetrahedron, 52, 3107 (1996).
56. A. V. R. Rao, M. K. Gurjar, D. V. Ramana and A. K. Chheda, Heterocycles, 43, 1 (1996).
57. Cs. Simon, S. Hosztafi and S. Makleit, Tetrahedron Letters, 34, 6475 (1993).
58. N. Yamazati and C. Kibayashi, J. Am. Chem. Soc., 111, 1396 (1989).
59. J. Mulzer, H. Dehmlow, J. Buschmann and P. Luger, J. Org. Chem., 57, 3194 (1992).
60. H. Ent, H. de Konig and W. N. Speckamp, Heterocycles, 27, 237 (1988).
61. B. P. Wijnberg and W. N. Speckamp, Tetrahedron Letters, 22, 5079 (1981).
62. J. Mittendorf, H. Hiemstra and W. N. Speckamp, Tetrahedron, 46, 4049 (1990).
63. J. M. Dener, D. J. Hart and S. Ramesh, J. Org. Chem., 53, 6022 (1988).
64. Cs. Simon, S. Hosztafi and S. Makleit, Synth. Commun., 22, 913 (1992).
65. Cs. Simon, S. Hosztafi and S. Makleit, Heterocycles, 38, 1347 (1994).
66. A. Garcia, L. Castedo and D. Dominguez, Tetrahedron Letters, 34, 1797 (1993).
67. T. S. Kaufman, Tetrahedron Letters, 37, 5329 (1996).
68. J. L. Ralbovsky, P. M. Scola, E. Sugino, C. Burgos-Garcia, S. M. Weinreb and M. Parvez, Heterocycles, 43, 1497 (1996).
69. K. Sestanj, E. Melenski and I. Jivorsky, Tetrahedron Letters, 35, 5417 (1994).
70. R. J. Fletcher, D. E. Hibbs, M. Hursthouse, C. Lampard, J. A. Murphy and S. J. Roome, J. Chem. Soc., Chem. Commun., 739 (1996).
71. M. Kizil, C. Lampard and J. A. Murphy, Tetrahedron Letters, 37, 2511 (1996).
72. J. A. Campbell and D. J. Hart, Tetrahedron Letters, 33, 6247 (1992).
73. J. A. Campbell and D. J. Hart, J. Org. Chem., 58, 2900 (1993).
74. R. C. Bernotas and R. V. Cube, Tetrahedron Letters, 32, 161 (1991).
75. D. M. Goldstein and P. Wipf, Tetrahedron Letters, 37, 739 (1996).
76. H. Ina, M. Ito and C. Kibayashi, J. Org. Chem., 61, 1023 (1996).
77. T. Tsunoda, F. Ozaki, N. Shirakata, Y. Tamaoka, H. Yamamoto and S. Itô, Tetrahedron Letters, 37, 2463 (1996).
78. D. L. Comins, H. Hong, J. K. Saha and G. Jianhua, J. Org. Chem., 59, 5120 (1994).
79. D. L. Comins, H. Hong and G. Jianhua, Tetrahedron Letters, 35, 5331 (1994).
80. J. Reisch, A. R. R. Rao and C. O. Usifoh, Monatsh. Chem., 125, 79 (1994).
81. J. H. van Maarseveen, E. H. H. Oberye, M. B. Bolster, H. W. Scheeren and C. G. Kruse, Recl. Trav. Chim. Pays-Bas, 114, 27 (1995).
82. M. A. Poelert, L. A. Hulshof and R. M. Kellog, Recl. Trav. Chim. Pays-Bas, 113, 355 (1994).
83. I. Fujii, H. Togame, M. Yamamoto, K. Kanematsu, I. Takayanagi and F. Konno, Chem. Pharm. Bull., 36, 2282 (1988).
84. K. Kanematsu, T. Yoshiyasu and M. Yoshida, Chem. Pharm. Bull., 38, 1441 (1990).
85. T. Sagara, S. Ozawa, E. Kushiyama, K. Koike, I. Takayanagi and K. Kanematsu, BioMed. Chem. Letters, 5, 1505 (1995).
86. Cs. Simon, S. Hosztafi and S. Makleit, (unpublished results).