Studies on the biomimetic preparation of the sarpagan ring system. Attempts to apply the spontaneous 'biogenetic-type cyclization' of van Tamelen to bond formation between C-5 and C-16 in the corynantheine series

Tetrahedron

Volumn 52, Issue 48, 1996, Pages 15225-15242

  Lounasmaa, Mauri ^a   Hanhinen, Pirjo ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030602267     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00928-3     Document Type: Article

References (42)

1. 1. van Tamelen, E. E.; Oliver, L. K., J. Am. Chem. Soc., 1970, 92, 2136-2137. See also van Tamelen, E. E., Acc. Chem. Res., 1968, 1, 111-120, van Tamelen, E. E.; Haarstad, V. B.; Orvis, R. L., Tetrahedron, 1968, 24, 687-704, Scott, A. I., Bioorg. Chem., 1974, 3, 398-429, van Tamelen, E. E.; Dorschel, C., Bioorg. Chem. 1976, 5, 203-228, Stöckigt, J., Tetrahedron Lett., 1979, 20, 2615-2618, and Schmidt, D.; Stöckigt, J., Planta Med., 1995, 61, 254-258.
2. 1. van Tamelen, E. E.; Oliver, L. K., J. Am. Chem. Soc., 1970, 92, 2136-2137. See also van Tamelen, E. E., Acc. Chem. Res., 1968, 1, 111-120, van Tamelen, E. E.; Haarstad, V. B.; Orvis, R. L., Tetrahedron, 1968, 24, 687-704, Scott, A. I., Bioorg. Chem., 1974, 3, 398-429, van Tamelen, E. E.; Dorschel, C., Bioorg. Chem. 1976, 5, 203-228, Stöckigt, J., Tetrahedron Lett., 1979, 20, 2615-2618, and Schmidt, D.; Stöckigt, J., Planta Med., 1995, 61, 254-258.
3. 1. van Tamelen, E. E.; Oliver, L. K., J. Am. Chem. Soc., 1970, 92, 2136-2137. See also van Tamelen, E. E., Acc. Chem. Res., 1968, 1, 111-120, van Tamelen, E. E.; Haarstad, V. B.; Orvis, R. L., Tetrahedron, 1968, 24, 687-704, Scott, A. I., Bioorg. Chem., 1974, 3, 398-429, van Tamelen, E. E.; Dorschel, C., Bioorg. Chem. 1976, 5, 203-228, Stöckigt, J., Tetrahedron Lett., 1979, 20, 2615-2618, and Schmidt, D.; Stöckigt, J., Planta Med., 1995, 61, 254-258.
4. 1. van Tamelen, E. E.; Oliver, L. K., J. Am. Chem. Soc., 1970, 92, 2136-2137. See also van Tamelen, E. E., Acc. Chem. Res., 1968, 1, 111-120, van Tamelen, E. E.; Haarstad, V. B.; Orvis, R. L., Tetrahedron, 1968, 24, 687-704, Scott, A. I., Bioorg. Chem., 1974, 3, 398-429, van Tamelen, E. E.; Dorschel, C., Bioorg. Chem. 1976, 5, 203-228, Stöckigt, J., Tetrahedron Lett., 1979, 20, 2615-2618, and Schmidt, D.; Stöckigt, J., Planta Med., 1995, 61, 254-258.
5. 1. van Tamelen, E. E.; Oliver, L. K., J. Am. Chem. Soc., 1970, 92, 2136-2137. See also van Tamelen, E. E., Acc. Chem. Res., 1968, 1, 111-120, van Tamelen, E. E.; Haarstad, V. B.; Orvis, R. L., Tetrahedron, 1968, 24, 687-704, Scott, A. I., Bioorg. Chem., 1974, 3, 398-429, van Tamelen, E. E.; Dorschel, C., Bioorg. Chem. 1976, 5, 203-228, Stöckigt, J., Tetrahedron Lett., 1979, 20, 2615-2618, and Schmidt, D.; Stöckigt, J., Planta Med., 1995, 61, 254-258.
6. 1. van Tamelen, E. E.; Oliver, L. K., J. Am. Chem. Soc., 1970, 92, 2136-2137. See also van Tamelen, E. E., Acc. Chem. Res., 1968, 1, 111-120, van Tamelen, E. E.; Haarstad, V. B.; Orvis, R. L., Tetrahedron, 1968, 24, 687-704, Scott, A. I., Bioorg. Chem., 1974, 3, 398-429, van Tamelen, E. E.; Dorschel, C., Bioorg. Chem. 1976, 5, 203-228, Stöckigt, J., Tetrahedron Lett., 1979, 20, 2615-2618, and Schmidt, D.; Stöckigt, J., Planta Med., 1995, 61, 254-258.
7. 1. van Tamelen, E. E.; Oliver, L. K., J. Am. Chem. Soc., 1970, 92, 2136-2137. See also van Tamelen, E. E., Acc. Chem. Res., 1968, 1, 111-120, van Tamelen, E. E.; Haarstad, V. B.; Orvis, R. L., Tetrahedron, 1968, 24, 687-704, Scott, A. I., Bioorg. Chem., 1974, 3, 398-429, van Tamelen, E. E.; Dorschel, C., Bioorg. Chem. 1976, 5, 203-228, Stöckigt, J., Tetrahedron Lett., 1979, 20, 2615-2618, and Schmidt, D.; Stöckigt, J., Planta Med., 1995, 61, 254-258.
8. 2. van Tamelen, E. E.; Oliver, L. K., Bioorg. Chem., 1976, 5, 309-326. See also Herlem, D.; Florès-Parra, A.; Khuong-Huu, F.; Chiaroni, A.; Riche, C., Tetrahedron, 1982, 38, 271-278.
9. 2. van Tamelen, E. E.; Oliver, L. K., Bioorg. Chem., 1976, 5, 309-326. See also Herlem, D.; Florès-Parra, A.; Khuong-Huu, F.; Chiaroni, A.; Riche, C., Tetrahedron, 1982, 38, 271-278.
10. 3. Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M., Tetrahedron, 1989, 45, 2683-2692.
11. 4. Jokela, R.; Halonen, M.; Lounasmaa, M., Tetrahedron, 1993, 49, 2567-2576.
12. 5. Jokela, R.; Halonen, M.; Lounasmaa, M., Heterocycles, 1994, 38, 189-196.
13. 6. Halonen, M.; Jokela, R.; Lounasmaa, M., Heterocycles, 1995, 41, 353-362.
14. 7. Lounasmaa, M.; Halonen, M.; Jokela, R., Heterocycles, 1995, 41, 807-816.
15. 8. Lounasmaa, M.; Koskinen, A., Tetrahedron Lett., 1982, 23, 349-352.
16. 9. Jokela, R.; Halonen, M.; Lounasmaa, M., Heterocycles, 1993, 36, 1115-1126.
17. 10. Lounasmaa, M.; Hanhinen, P., Heterocycles, 1996, 43, 1981-1989.
18. 11. Lounasmaa, M.; Tamminen, T., Tetrahedron, 1991, 47, 2879-2894.
19. 12. Lounasmaa, M., Synthetic Studies in the Field of Indole Alkaloids, in "Studies in Natural Products Chemistry" (Atta-ur-Rahman, Ed.), Vol. 1, Elsevier, Amsterdam, 1988, pp. 89-122.
20. 13. Lounasmaa, M., Synthetic Studies in the Field of Indole Alkaloids, Part 2., in "Studies in Natural Products Chemistry" (Atta-ur-Rahman, Ed.), Vol. 14, Elsevier, Amsterdam, 1994, pp. 703-730.
21. 14. Southon, I. W.; Buckingham, J., in "Dictionary of Alkaloids", London, Chapman and Hall, London, 1989.
22. 15. Koskinen, A.; Lounasmaa, M., The Sarpagine-Ajmaline Group of Indole Alkaloids, in "Progress in the Chemistry of Organic Natural Products" (Hertz, W.; Grisebach, H.; Kirby, G. W., Eds.), Vol. 43, Springer Verlag, Wien - New York, 1983, pp. 267-346.
23. 16. Sakai, S.; Wongseripipatana, S.; Ponglux, D.; Yokota, M.; Ogata, K.; Takayama, H.; Aimi, N., Chem. Pharm. Bull., 1987, 35, 4668-4671.
24. 17. Schun, Y.; Cordell, G. A., Phytochemistry, 1987, 26, 2875-2876.
25. 18. Neither could compound 23 be obtained from compound 22 by treatment with an external base.
26. 13C-Nmr data of compounds (i), (ii), and (iii) are given below. (formula presented)
27. 20. van Tamelen, E. E.; Foltz, R. L., J. Am. Chem. Soc. , 1969, 91, 7372-7377.
28. 34 in his studies on intramolecular cyclization between an iminium salt and a nucleophilic carbon, has shown that in certain cases when the activating two ester groups in a malonate nucleophile were replaced by a single, electron withdrawing group, the yields in the reversible cyclization process were higher because of decreasing steric strain in the product.
29. 22. Grierson, D. S.; Harris, M.; Husson, H.-P., J. Am. Chem. Soc., 1980, 102, 1064-1082.
30. 23. Harris, M.; Grierson, D. S.; Riche, C.; Husson, H.-P., Tetrahedron Lett., 1980, 21, 1957-1960.
31. 24. Guibe, F.; Grierson, D. S.; Husson, H.-P., Tetrahedron Lett., 1982, 23, 5055-5058.
32. 25. Jokela, R.; Karvinen, E.; Tolvanen, A.; Lounasmaa, M., Tetrahedron, 1988, 44, 2367-2375.
33. 26. Lounasmaa, M.; Jokela, R., Tetrahedron 1989, 45, 3975-3992.
34. 27. Lounasmaa, M.; Jokela, R.; Tirkkonen, B.; Miettinen, J.; Halonen, M., Heterocycles, 1992, 34, 321-339.
35. 28. Tirkkonen, B.; Miettinen, J.; Salo, J.; Jokela, R.; Lounasmaa, M., Tetrahedron, 1994, 50, 3537-3556.
36. 29. Hanhinen, P.; Nurminen, T.; Jokela, R.; Lounasmaa, M., Heterocycles, 1994, 38, 2027-2044.
37. 30. Lounasmaa, M.; Jokela, R.; Hanhinen, P.; Miettinen, J.; Salo, J., Tetrahedron, 1994, 50, 9207-9222.
38. 31. Lounasmaa, M; Jokela, R.; Hanhinen, P.; Laine, C.; Anttila, U., Heterocycles, 1996, 43, 1699-1712.
39. 32. The most characteristic signal indicating the presence of a cyano group at C-5β (compounds 29 and 32) is that of C-6 at -26.5 ppm (Cf. Figure 1).
40. 33. Note! The formula given for pericyclivine (i)(vide supra) on p. 836 of Ref. 14 is erroneous.
41. 34. Bates, H. A.; Rapoport, H.; J. Am. Chem. Soc., 1979, 101, 1259-1265. See also, Rapoport, H., Stereospecific Synthesis with Amino Acids and Iminium Salts, in "Stereoselective Synthesis of Natural Products", (Bartmann, W.; Winterfeldt, E., Eds.), Excerpta Medica, Amsterdam-Oxford, 1979, pp. 37-49.
42. 34. Bates, H. A.; Rapoport, H.; J. Am. Chem. Soc., 1979, 101, 1259-1265. See also, Rapoport, H., Stereospecific Synthesis with Amino Acids and Iminium Salts, in "Stereoselective Synthesis of Natural Products", (Bartmann, W.; Winterfeldt, E., Eds.), Excerpta Medica, Amsterdam-Oxford, 1979, pp. 37-49.