Recent progress in the chemistry of monoterpenoid indole alkaloids derived from secologanin

Abstract

References

1. Alkaloids: Chemistry and Pharmacology, Vol. 49, ed. G. A. Cordell, Academic Press, London, 1997.
2. ‘The Indole Alkaloids’, G. W. Gribble, in Rodd's Chemistry of Carbon Compounds, 2nd edn., ed. M. Sainsbury, 1997, vol. 69, p. 4.
3. C. Simon, S. Hosztafi and S. Makleit, J. Heterocycl. Chem., 1997, 34, 349.
4. S. Hosztafi, Pharmazie, 1997, 52, 546.
5. S. F. Martin, Pure Appl. Chem., 1997, 69, 571.
6. M. Amat, S. Hadida, G. Pshenichnyi and J. Bosch, J. Org. Chem., 1997, 62, 3158.
7. E. M. Anam, Indian J. Chem., Sect. B., 1997, 36, 54.
8. D. Arbain, L. T. Byrne, Dachriyanus and M. V. Sargent, Aust. J. Chem., 1997, 50, 1109.
9. D. Arbain, L. T. Byrne, Dachriyanus, N. Evrayoza and M. V. Sargent, Aust. J. Chem., 1997, 50, 1111.
10. H. Achenbach and M. Benirschke, Phytochemistry, 1997, 44, 1387.
11. L. F. Tietze, J. Bachmann, J. Wichmann, Y. Zhou and T. Raschke, Liebigs Ann./Recl., 1997, 881.
12. M. Ihara, A. Katsumata and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1997, 991.
13. M. Ihara, N. Taniguchi and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1997, 365.
14. H. Takayama, F. Watanabe, K. Kitajima and N. Aimi, Tetrahedron Lett., 1997, 38, 5307.
15. H. Takayama, Y. IiMura, M. Kitajima, N. Aimi, K. Konno, H. Inoue, M. Fujiwara, T. Mizuta, T. Yokota, S. Shigeta, K. Tokuhisa, Y. Hanasaki and K. Katsuura, Bioorg. Med. Chem. Lett., 1997, 7, 3145.
16. M. Lounasmaa, J. Miettinen, P. Hanhinen and R. Jokela, Tetrahedron Lett., 1997, 38, 1455.
17. M. Lounasmaa, R. Jokela, P. Hanhinen and U. Anttila, Heterocycles, 1997, 45, 779.
18. R. T. Brown and J. Leonard, Tetrahedron Lett., 1977, 4251.
19. R. T. Brown, in Indole and Biogenetically Related Alkaloids, ed. J. D. Phillipson and M. H. Zenk, Academic Press, London, 1980, pp. 171–184.
20. M. Lounasmaa and P. Hanhinen, Heterocycles, 1997, 45, 1529.
21. M. Ohba, H. Kubo, T. Fujii, H. Ishibashi, M. V. Sargent and D. Arbain, Tetrahedron Lett., 1997, 38, 6697.
22. A. W. M. Lee, W. H. Chan and T. Mo, Tetrahedron Lett., 1997, 38, 3001.
23. J. Leonard, A. B. Hague and M. F. Jones, Tetrahedron Lett., 1997, 38, 3071.
24. J. Leonard, S. P. Fearnley, A. B. Hague, G. Wong and M. F. Jones, Tetrahedron Lett., 1997, 38, 3069.
25. S. Hanessian, J. Pan, A. Carnell, H. Bouchard and L. Lesage, J. Org. Chem., 1997, 62, 465.
26. T.-S. Kam, K.-T. Nyeoh, K.-M. Sim and K. Yoganathan, Phytochemistry, 1997, 45, 1303.
27. T. Fukuyama and G. Liu, Pure Appl. Chem., 1997, 69, 501.
28. S. Atarashi, J.-K. Choi, D.-C. Ha, D. J. Hart, D. Kuzmich, C.-S. Lee, S. Ramesh and S. C. Wu, J. Am. Chem. Soc., 1997, 119, 6226.
29. W. G. Beyersbergen van Hengouwen and H. Hiemstra, J. Org. Chem., 1997, 62, 8862.
30. P. D. Bailey, I. D. Collier, S. P. Hollinshead, M. H. Moore, K. M. Morgan, D. I. Smith and J. M. Vernon, J. Chem. Soc., Perkin Trans. 1, 1997, 1209.
31. P. Yu, T. Wang, F. Yu and J. M. Cook, Tetrahedron Lett., 1997, 38, 6819.
32. M. L. Bennasar, B. Vidal and J. Bosch, J. Org. Chem., 1997, 62, 3597.
33. N. Harda, T. Kawaguchi, I. Inoue, M. Ohashi, K. Oda, T. Hashiyama and K. Tsujihara, Chem. Pharm. Bull., 1997, 45, 134.
34. R. A. Jones, J. Pastor, J. Siro and T. N. Voro, Tetrahedron, 1997, 53, 479.
35. M. Ishikura, T. Yaginuma, I. Agata, Y. Miwa, R. Yanada and T. Taga, Synlett, 1997, 214.
36. M. Saito, M. Kawamura, K. Hiroya and K. Ogasawara, Chem. Commun., 1997, 765.
37. M. H. Schmitt and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 1474.
38. G. Hugel, D. Royer, L. Le Men-Olivier, B. Richard, M.-J. Jacquier and J. Lévy, J. Org. Chem., 1997, 62, 578.
39. G. Hugel and J. Lévy, Tetrahedron Lett., 1997, 38, 4553.
40. P. Thepenier, M. J. Jacquier, G. Massiot, L. Le Men-Oliver and C. Delaude, Bull. Soc. R. Sci. Liege, 1997, 66, 341.
41. M. E. Kuehne and F. Xu, J. Org. Chem., 1997, 62, 7950.
42. C. Mirand, M. Papa, D. Cartier and J. Lévy, Tetrahedron Lett., 1997, 38, 2263.
43. J. Bonjoch, D. Solé, S. García-Rubio and J. Bosch, J. Am. Chem. Soc., 1997, 119, 7230.
44. M. Amat, M.-D. Coll, J. Bosch, E. Espinosa and E. Molins, Tetrahedron: Asymmetry, 1997, 8, 935.
45. T.-S. Kam and K. Yoganathan, Phytochemistry, 1997, 46, 785.
46. T.-S. Kam, K. Yoganathan and C.-H. Chuah, Phytochemistry, 1997, 46, 632.
47. K. Okada, K. Murakami and H. Tanino, Tetrahedron, 1997, 53, 14247.
48. M. Ibrahim-Quali, M.-E. Sinibaldi, Y. Troin, D. Guillaume and J.-C. Gramain, Tetrahedron, 1997, 53, 16083.
49. B. David, T. Sévenet, O. Thoison, K. Awang, M. Païs, M. Wright and D. Guénard, Bioorg. Med. Chem. Lett., 1997, 7, 2155.
50. G. Kalaus, I. Juhász, I. Greiner, M. Kajtár-Peredy, J. Brlik, L. Szabó and C. Szántay, J. Org. Chem., 1997, 62, 9188.
51. G. Lewin and C. Schaeffer, Heterocycles, 1997, 45, 475.
52. B. Danieli, G. Lesma, M. Martinelli, D. Passarella and A. Silvani, J. Org. Chem., 1997, 62, 6519.
53. S. Uzir, A. M. Mustapha, A. H. A. Hadi, K. Awang, C. Wiart, J.-F. Gallard and M. Pais, Tetrahedron Lett., 1997, 38, 1571.
54. A. G. Schultz, W. P. Malachowski and Y. Pan, J. Org. Chem., 1997, 62, 1223.
55. A. G. Schultz and L. Pettus, J. Org. Chem., 1997, 62, 6855.
56. J. E. D. Barton and J. Harley-Mason, J. Chem. Soc., Chem. Commun., 1967, 298.
57. D. Desmaële, K. Mekouar and J. d'Angelo, J. Org. Chem., 1997, 62, 3890.
58. J. C. F. Alves, A. B. C. Simas, P. R. R. Costa and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963.
59. L. Szabó, E. Szentirmay, E. Baitz-Gács, G. Kalaus and C. Szántay, Tetrahedron Lett., 1997, 38, 115.
60. A. Danscó, M. Kajtár-Peredy and C. Szántay, J. Heterocycl. Chem., 1997, 34, 1267.
61. E. Szentirmay, L. Szabó, G. Kalaus, P. Holontis, M. Hollosi and C. Szántay, J. Nat. Prod., 1997, 10, 257.
62. B. Lygo and P. G. Wainwright, Tetrahedron Lett., 1997, 38, 8595.
63. E. J. Corey, F. Xu and M. C. Noe, J. Am. Chem. Soc., 1997, 119, 12414.
64. B. Lygo, J. Crosby, T. R. Lowdon and P. G. Wainwright, Tetrahedron Lett., 1997, 38, 2343.
65. M. D. Drew, N. J. Lawrence, W. Watson and S. A. Bowles, Tetrahedron Lett., 1997, 38, 5857.
66. N. Moitessier, F. Chretien and Y. Chapleur, Tetrahedron: Asymmetry, 1997, 8, 2889.
67. C. E. Song, J. W. Yang and H. J. Ha, Tetrahedron: Asymmetry, 1997, 8, 841.
68. E. Nandanan, A. Sudalai and T. Ravindranathan, Tetrahedron Lett., 1997, 38, 2577.
69. A. Baiker, J. Mol. Catal. A.: Chem., 1997, 115, 473.
70. H. U. Blaser, H. P. Jalett, M. Muller and M. Studer, Catal. Today, 1997, 37, 441.
71. H. Bonnemann and G. A. Braun, Chem. Eur. J., 1997, 3, 1200.
72. G. Z. Wang, T. Mallat and A. Baiker, Tetrahedron: Asymmetry, 1997, 8, 2133.
73. M. Schurch, O. Schwalm, T. Mallat, J. Weber and A. Baiker, J. Catal., 1997, 169, 275.
74. J. U. Kohler and J. S. Bradley, Catal. Lett., 1997, 45, 203.
75. T. Mallat, M. Bodmer and A. Balker, Catal. Lett, 1997, 44, 95.
76. R. L. Augustine and S. K. Tanielyan, J. Mol. Catal. A: Chem., 1997, 118, 79.
77. T. H. A. Silva, A. B. Oliveira and W. B. DeAlmeida, Struct. Chem., 1997, 8, 95.
78. T. H. A. Silva, A. B. Oliveira and W. B. DeAlmeida, Bioorg. Med. Chem., 1997, 5, 353.
79. R. A. Daines, K. K. C. Sham, J. J. Taggart, W. D. Kingsbury, J. Chan, A. Breen, J. Disa and N. Aiyar, Boorg. Med. Chem. Lett., 1997, 7, 2673.
80. J. Thiel and P. Fiedorow, J. Mol. Struct. (THEOCHEM), 1997, 405, 219.
81. H. Brunner and J. Bugler, Bull. Soc. Chim. Belg., 1997, 106, 77.
82. P. Langer and H. M. R. Hoffmann, Tetrahedron, 1997, 53, 9145.
83. S. J. Rowan, D. G. Hamilton, P. A. Brady and J. K. M. Sanders, J. Am. Chem. Soc., 1997, 119, 2578.
84. S. J. Rowan and J. K. M. Sanders, Chem. Commun., 1997, 1407.
85. B. Das, S. P. Rao, A. Kashinatham and K. V. N. S. Srinivas, Indian J. Chem., Sect. B., 1997, 36, 208.
86. Z. Cao, Synth. Commun., 1997, 27, 2013.
87. N. Aimi, H. Hoshino, M. Nishimura, S. Sakai and J. Haginiwa, Tetrahedron Lett., 1990, 31, 5169.
88. M. Kitajima, S. Masumoto, H. Takayama and N. Aimi, Tetrahedron Lett., 1997, 38, 4255.
89. M. Kitajima, M. Nakamura, H. Takayama, K. Saito, J. Stöckigt and N. Aimi, Tetrahedron Lett., 1997, 38, 8997.
90. M. A. Ciufolini and F. Roschangar, Tetrahedron, 1997, 53, 11049.
91. N. Murata, T. Sugihara, Y. Kondo and T. Sakamoto, Synlett, 1997, 298.
92. K. Tagami, S. Takagi, S. Sano, M. Shiro and Y. Nagao, Heterocycles, 1997, 45, 1663.
93. H. Josien and D. P. Curran, Tetrahedron, 1997, 53, 8881.
94. I. Candiani, A. Bedeschi, W. Carbri, F. Zarini, G. Visentin, L. Capolongo, C. Geroni and M. Ciomei, Bioorg. Med. Chem. Lett., 1997, 7, 847.
95. O. Lavergne, L. Lesuer-Ginot, F. P. Rodas and D. C. H. Bigg, Bioorg. Med. Chem. Lett., 1997, 7, 2235.
96. T.-S. Kam, K. Yoganathan, H.-Y. Li and N. Harada, Tetrahedron, 1997, 53, 12661.
97. T.-S. Kam and K. Yoganathan, Nat. Prod. Lett., 1997, 10, 69.
98. K. X. Yan and X. Z. Feng, Chin. Chem. Lett., 1997, 8, 313.
99. I. Tabakovic, E. Gunic and I. Juranic, J. Org. Chem., 1997, 62, 947.
100. J. Fahy, A. Duflos, J.-P. Ribet, J.-C. Jacquesy, C. Berrier, M.-P. Jouannetaud and F. Zunino, J. Am. Chem. Soc., 1997, 119, 8576.
101. J. Fahy, A. Duflos, J.-P. Ribet, J.-C. Jacquesy, C. Berrier, M.-P. Jouannetaud, P. Marie, Y. Vidal and F. Zunino, FR 2,737,208 (Chem. Abstr., 1997, 293482d).
102. K. Hirata, S. Duangteraprecha, E. Morihara, M. Honda, T. Akagi, M. Nakae, H. Katayama and K. Miyamoto, Biotechnol. Lett., 1997, 19, 53.