Total syntheses of macrocyclic marine alkaloids, haliclamines A and B: A convenient and expeditious assembly of 3-substituted pyridine derivatives with different alkyl chains to the bispyridinium macrocycle

Tetrahedron

Volumn 54, Issue 40, 1998, Pages 12197-12214

  Morimoto, Yoshiki ^a   Yokoe, Chiho ^a   Kurihara, Hajime ^a   Kinoshita, Takamasa ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; DIHYDROPYRIDINE DERIVATIVE; HALICLAMINE A DERIVATIVE; HALICLAMINE B DERIVATIVE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0032192351     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00752-2     Document Type: Article

References (28)

1. 1. Andersen, R. J.; van Soest, R. W. M.; Kong, F. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; New York: Pergamon, 1996; Vol. 10, pp. 301-355.
2. 2. Kobayashi, J.; Tsuda, M. J. Synth. Org. Chem. Jpn. 1997, 55, 1114-1123.
3. 3. Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G. J. Am. Chem. Soc. 1986, 108, 6404-6405.
4. 4. Baldwin, J. E.; Whitehead, R. C. Tetrahedron Lett. 1992, 33, 2059-2062.
5. 5. Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron 1994, 50, 6137-6144.
6. 6. Rodríguez, J.; Crews, P. Tetrahedron Lett. 1994, 35, 4719-4722.
7. 7. Kong, F.; Andersen, R. J.; Allen, T. M. J. Am. Chem. Soc. 1994, 116, 6007-6008.
8. 8. Charan, R. D.; Garson, M. J.; Brereton, I. M.; Willis, A. C.; Hooper, J. N. A. Tetrahedron 1996, 52, 9111-9120.
9. 9. Jaspars, M.; Pasupathy, V.; Crews, P. J. Org. Chem. 1994, 59, 3253-3255.
10. 10. Baldwin, J. E.; Claridge, T. D. W.; Heupel, F. A.; Whitehead, R. C. Tetrahedron Lett. 1994, 35, 7829-7832.
11. 11. Gil, L.; Gateau-Olesker, A.; Marazano, C.; Das, B. C. Tetrahedron Lett. 1995, 36, 707-710.
12. 12. Gil, L.; Gateau-Olesker, A.; Wong, Y.-S.; Chernatova, L.; Marazano, C.; Das, B. C. Tetrahedron Lett. 1995, 36, 2059-2062.
13. 13. Gil, L.; Baucherel, X.; Martin, M.-T.; Marazano, C.; Das, B. C. Tetrahedron Lett. 1995, 36, 6231-6234.
14. 14. Baldwin, J. E.; Claridge, T. D. W.; Culshaw, A. J.; Heupel, F. A.; Smrcková, S.; Whitehead, R. C. Tetrahedron Lett. 1996, 37, 6919-6922.
15. 15. Baldwin, J. E.; Bischoff, L.; Claridge, T. D. W.; Heupel, F. A.; Spring, D. R.; Whitehead, R. C. Tetrahedron 1997, 53, 2271-2290.
16. 16. For a review on syntheses and synthetic approaches toward manzamine alkaloids, see: Magnier, E.; Langlois, Y. Tetrahedron 1998, 54, 6201-6258.
17. 17. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hirota, H. Tetrahedron Lett. 1989, 30, 6891-6894.
18. 18. Fusetani, N.; Asai, N.; Matsunaga, S.; Honda, K.; Yasumuro, K. Tetrahedron Lett. 1994, 35, 3967-3970.
19. 19. The total syntheses of cyclostellettamines A-F have been reported by other groups. See: (a) Anan, H.; Seki, N.; Noshiro, O.; Honda, K.; Yasumuro, K.; Ozasa, T.; Fusetani, N. Tetrahedron 1996, 52, 10849-10860.
20. (b) Wanner, M. J.; Koomen, G.-J. Eur. J. Org. Chem. 1998, 889-895.
21. 20. For our preliminary report on total synthesis of haliclamine A (1), see: Morimoto, Y.; Yokoe, C. Tetrahedron Lett. 1997, 38, 8981-8984.
22. 21. Solladié, G.; Somny, F.; Colobert, F. Tetrahedron: Asymmetry 1997, 8, 801-810.
23. 2+, 0 °C → rt, 5 h, 94%; 2) n-BuLi, THF, -15 °C, 30 min.
24. 23. Torisawa, Y.; Hashimoto, A.; Nakagawa, M.; Seki, H.; Hara, R.; Hino, T. Tetrahedron 1991, 47, 8067-8078.
25. 24. Davies-Coleman, M. T.; Faulkner, D. J.; Dubowchik, G. M.; Roth, G. P.; Polson, C.; Fairchild, C. J. Org. Chem. 1993, 58, 5925-5930.
26. 25. Wenkert, E.; Massy-Westropp, R. A.; Lewis, R. G. J. Am. Chem. Soc. 1962, 84, 3732-3736.
27. 26. Lyle, R. E.; Anderson, P. S. Adv. Heterocycl. Chem. 1966, 6, 45-93.
28. 27. Baldwin et al. have reported that the conversion of bispyridinium macrocycle such as 44 into the bisdihydropyridine derivative 3 is possible via reduction and oxidation (reference 14).