Synthetic studies on manzamine A: An efficient synthesis of the bicyclic compound leading to the formation of the tetracyclic ABCE ring subunit I (I)

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2597-2600

  Li, Shouming ^a   Yamamura, Shosuke ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; MANYGEEN; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; ISOMERISM; REACTION ANALYSIS;

EID: 0032559953     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00278-0     Document Type: Article

References (31)

1. 1. a) Sakai, R.; Riga, T. J. Am. Chem. Soc., 1986, 108, 6404;
2. b) Nakamura, H; Deng, S.; Kobayashi, J.; Ohizumi, Y.; Tomotake, Y.; Matsuzaki, T.; Midori, K.; Hirata, Y. Tetrahedron Lett., 1987, 28, 621.
3. 2. a) Brands, K. M. J.; Pandit, U. K. ibid., 1989, 30, 1423; Heterocycles, 1990, 30, 257;
4. 2. a) Brands, K. M. J.; Pandit, U. K. ibid., 1989, 30, 1423; Heterocycles, 1990, 30, 257;
5. b) Brands, K. M. J.; Meckel, A. A. P; Pandit, U. K. Tetrahedron, 1991, 47, 2005;
6. c) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett., 1994, 35, 3191;
7. d) Imbroisi, D. O.; Simpkins, N. S. ibid., 1989, 30, 4309;
8. c) Martin, S. F.; Redin, T.; Hino, Y. ibid., 1991, 32, 6481;
9. f) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. ibid., 1994, 35, 691;
10. g) Leonard, J.; Feamley, S. P.; Hickey, D. M. B. Synlett., 1992, 272;
11. h) Marko, I.E.; Chesney, A. ibid., 1992, 275;
12. i) Nakagawa, M.; Lai, Z.; Torisawa, Y.; Hino, T. Heterocycles, 1990, 37, 999;
13. j) Torisawa, Y.; Nakagawa, M.; Arai, H.; Lai, Z.; Hino, T.; Nakata, T.; Ohishi, T. Tetrahedron Lett., 1990, 31, 3195;
14. k) Torisawa, Y.; Nakagawa, M.; Hosaka, T.; Tanabe, K.; Lai, Z.; Ogata, K.; Nakata, T.; Ohishi, T. J. Org. Chem., 1992, 57, 5741;
15. l) Nakagawa, M.; Torisawa, Y.; Hosaka, T.; Tanabe, K; Date, T.; Okamura, K.; Hino, T. Tetrahedron Lett., 1993, 34, 4543;
16. m) Hart, D. J.; Mekkinney, J.A. ibid., 1989, 30, 2611;
17. n) Campbell, J. A.; Hart, D.J. ibid., 1992, 33, 6247;
18. o) Kamenecka, T. M.; Overman, L. E. ibid., 1994, 35, 4297;
19. p) Clark, J. S.; Hodgson, P. B. ibid., 1995, 36, 2519;
20. q) Magnier, E.; Langlois, Y. ibid., 1995, 36, 9475;
21. r) Winkler, D.J.; Stelmach, I E.; Axten, H. ibid., 1996, 37, 4317;
22. s) Winkler, J. D.; Siegel, M. G.; Stelmach, H. E. ibid., 1993, 34, 6509;
23. t) Li, S.; Kosemura, S.; Yamamura, S. Tetrahedron Lett. ,1994, 35, 8217.
24. 3. Li, S.; Ohba, S.; Kosemura, S.; Yamamura, S. Tetrahedron Lett., 1996, 37, 7365; Li, S.; Yamamura, S.; Hosomi, H.; Ohba, S. to be published.
25. 3. Li, S.; Ohba, S.; Kosemura, S.; Yamamura, S. Tetrahedron Lett., 1996, 37, 7365; Li, S.; Yamamura, S.; Hosomi, H.; Ohba, S. to be published.
26. 4. The spectral data for the new compounds cited herein are in accord with the structure assigned.
27. 5. Dixon, A. J.; Talor, R. J. K.; Helquist, P.; J. Org. Chem., 1981, 46, 407.
28. 6. a) Bal, S. A.; Marfat, A.; Helquist, P. J. Org., Chem., 1982, 47, 5045;
29. b) Brallesani, D. N.; Heathcock, C. H. ibid., 1975, 40, 2165.
30. 7. Fieser, M.; Fieser, L. F. "Reagent for Organic Synthesis" 1974, Vol. 4, P16.
31. 8. Mitsunobu, O. Synthesis, 1981, 1.