Reaction of chiral nucleophiles with pyridinium compounds. Total synthesis of the indole alkaloids (-)-isovallesiachotamine and (+)-vallesiachotamine

Liebigs Annales

Volumn , Issue 3, 1996, Pages 349-355

  Amann, Robert ^a   Arnold, Karen ^a   Spitzner, Dietrich ^a   Majer, Zsuzsanna ^b,c   Snatzke, Günther ^b  

^a UNIVERSITY OF HOHENHEIM   (Germany)

^b RUHR UNIVERSITY BOCHUM   (Germany)

^c EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

(+) Vallesiachotamine; ( ) Isovallesiachotamine; Diastereoselective synthesis; Indole alkaloids

Indexed keywords

EID: 33748909888     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960309     Document Type: Article

References (60)

1. E. Wenkert, Pure Appl. Chem. 1981, 53, 1271-1276;
2. E. Wenkert, T. D. J. Halls, G. Kunesch, K. Orito, R. E. Stephens, W. A. Temple, J. S. Yadav, J. Am. Chem. Soc. 1979, 101, 5370-5376.
3. M.-E. Bennasar, E. Zulaica, J.-M. Jiménez, J. Bosch, Tetrahedron Lett. 1990, 31, 747-750.
4. For a review see: M.-E. Bennasar, R. Eavilla, M. Alvarez, J. Bosch, Heterocycles 1988, 27, 789-824.
5. E. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170;
6. Angew. Chem. Int. Ed. Engl. 1993, 32, 131.
7. P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry (Ed.: J. E. Baldwin), Organic Chemistry Series, vol. 1, Pergamon Press, Oxford, New York, Toronto, Sydney, Paris, Frankfurt, 1984, p. 211-221.
8. H. Waldmann, Synlett 1995, 133-141;
9. M. Eounasmaa, E. Karvinen, Tetrahedron 1991, 47, 6371-6380;
10. E. W. Baxter, D. Labaree, H. E. Ammon, P. S. Mariano, J. Am. Chem. Soc. 1990, 112, 7682-7692;
11. G. Stork, Pure Appl. Chem. 1989, 61, 439-442;
12. S. Chao, F.-A. Kunng, J.-M. Gu, H. E. Ammon, P. S. Mariano, J. Org. Chem. 1984, 49, 2708-2711;
13. R. Grigg, H. Q. Nimal Gunaratne, E. McNaghrten, J. Chem. Soc., Perkin Trans. 1, 1983, 185-187;
14. H. Ernst, B. Hauser, E. Winterfeldt, Chem. Ber. 1981, 114, 1894-1906.
15. D. Spitzner, K. Arnold, J. J. Stezowski, T. Hildenbrand, S. Henkel, Chem. Ber. 1989, 122, 2027-2029;
16. K. Akiba, Y. Nishihara, M. Wada, Tetrahedron Lett. 1983, 24, 5269-5272.
17. A. I. Meyers, T. Oppenlaender, J. Am. Chem. Soc. 1986, 108, 1989-1996.
18. P. Mangeney, R. Gosmini, A. Alexakis, Tetrahedron Lett. 1991, 32, 3981-3984;
19. R. Gosmini, P. Mangeney, A. Alexakis, M. Commerçon, J.-F. Normant, Synlett 1991, 111-113;
20. S. Raussou, R. Gosmini, P. Mangeney, A. Alexakis, M. Commerçon, Tetrahedron Lett. 1994, 30, 5433-5436.
21. G. Quinkert, U. Schwartz, H. Stark, W.-D. Weber, F. Adam, H. Baier, G. Frank, G. Dürner, Liebigs Ann. Chem. 1982, 1999-2040.
22. F. Bohlmann, Chem. Ber. 1958, 91, 2157-2167.
23. Biogenetic numbering is applied according to: J. Le Men, W. I. Taylor, Experientia 1965, 21, 508-510.
24. D. Seebach, R. Imwinkelried, G. Stucky, Angew. Chem. 1986, 98, 182-183;
25. Angew. Chem. Int. Ed. Engl. 1986, 25, 178.
26. D. Seebach, R. Imwinkelried, G. Stucky, Helv. Chim. Acta 1987, 70, 448-464.
27. 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, 3645-3655.
28. E. Wenkert, E. C. Angell, J. Drexler, P. D. R. Moeller, J. St. Pyrek, Y.-J. Shi, M. Sultana, Y. D. Vankar, J. Org. Chem. 1986, 51, 2995-3000.
29. A. T. Nielsen, J. Org. Chem. 1957, 22, 1539-1548.
30. [6]).
31. L. Bartlett, N. J. Dastoor, J. Hrebek jr., W. Klyne, H. Schmid, G. Snatzke, Helv. Chim. Acta 1971, 54, 1238-1254.
32. D. Seebach, V. Prelog, Angew. Chem. 1982, 94, 696-702;
33. Angew. Chem. Int. Ed. Engl. 1982, 21, 654.
34. Abstracted from: R. Amann, Ph. D. Thesis, University of Hohenheim, 1992.
35. Short communication previously published: R. Amann, D. Spitzner, Angew. Chem. 1991, 103, 1373-1374;
36. Angew. Chem. Int. Ed. Engl. 1991, 30, 1320-1321.
37. J. D. Phillipson, M. H. Zenk, Indole and Biogenetically Related Alkaloids, Academic Press, New York, 1980;
38. L.-F. Tietze, Angew. Chem. 1983, 95, 840-853;
39. Angew. Chem. Int. Ed. Engl. 1983, 22, 828.
40. A. Walser, C. Djerassi, Heb. Chim. Acta 1965, 48, 391-404;
41. C. Djerassi, H. J. Monteiro, A. Walser, L. J. Durham, J. Am. Chem. Soc. 1966, 88, 1792-1798;
42. S. Mukhopadhyay, G. A. Handy, S. Funayama, G. A. Cordell, J. Nat. Prod. 1981, 44, 696-700;
43. H. Achenbach, C. Renner, I. Addae-Mensah, Planta Med. 1982, 46, 88-90;
44. T. A. van Beek, R. Verpoorte, A. Baerheim Svendsen, Planta Med. ibid. 1983, 47, 83-86;
45. Atta-ur-Rahman, S. Malik, J. Nat. Prod. 1984, 47, 388-389;
46. M. Sauerwein, K. Shimomura, Phytochemistry 1990, 29, 3377-3379;
47. M. Sauerwein, K. Ishimaru, K. Shimomura, Phytochemistry ibid. 1991, 30, 1153-1155.
48. P. G. Waterman, S. Zhong, Planta Med. 1982, 45, 28-30.
49. N. Aimi, T. Shito, K. Fukushima, Y. Itai, C. Aoyama, K. Kunisawa, S. Sakai, J. Haginiwa, K. Yamasaki, Chem. Pharm. Bull. 1982, 30, 4046-4051.
50. R. I. Geran, N. H. Greenberg, M. M. Macdonald, A. M. Schumacher, B. J. Abbott, Cancer Chemother. Rep. 1972, 3, 1-103.
51. D. Spitzner, E. Wenkert, Angew. Chem. 1984, 96, 972 + 975;
52. Angew. Chem. Int. Ed. Engl. 1984, 23, 984-985;
53. D. Spitzner, T. Zaubitzer, Y.-J. Shi, E. Wenkert, J. Org. Chem. 1988, 53, 2274-2278.
54. C. Djerassi, H. J. Monteiro, A. Walser, L. J. Durham, J. Am. Chem. Soc. 1966, 88, 1792-1798.
55. Molecular mechanics (MM2) calculations using PCMODEL, Serena Software, or ChemX, Chemical Design Ltd., Chipping Norton, England, supported this assumption.
56. K. T. D. De Silva, G. N. Smith, K. E. H. Warren, J. Chem. Soc., Chem. Commun. 1971, 905-907.
57. P. G. Waterman, S. Zhong, Planta Med. 1982, 45, 28-30.
58. We thank Prof. Dr. G. Höfle, GBF, Braunschweig, for samples and spectra.
59. G. Helmchen, Anhang zur Habilitationsschrift, Univ. Stuttgart, 1980.
60. The IUPAC rules are applied to the names of the compounds.