Total syntheses of carazostatin and hyellazole by allene-mediated electrocyclic reaction

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2593-2596

  Choshi, Tominari ^a   Sada, Takuya ^a   Fujimoto, Hiroyuki ^a   Nagayama, Chizu ^a   Sugino, Eiichi ^a   Hibino, Satoshi ^a  

^a FUKUYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARAZOSTATIN; HYELLAZOLE; SCAVENGER; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029993479     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00378-4     Document Type: Article

References (41)

1. For recent reviews, see: (a) Chakraborty, D. P.; Roy, S. in Prog. Chem. Org. Nat. Prod., Vol. 57; Herz, W.; Grisebach, H.; Kirby, G. W.; Tamm, C. Eds.; Springer: Wien, 1991, p. 71.
2. (b) D. P. Chakraborty, in The Alkaloids, Vol. 44; A. Brossi, Ed.; Academic: New York, 1993, p. 257.
3. For the isolation of hyellazole, see: Cardellina II, J. H.; Kirkup, M. P.; Moore, R. E.; Mynderse, J. S.; Seff, K.; Simmons, C. J. Tetrahedron Lett. 1979, 4915.
4. For previous syntheses of hyellazole, see: (a) Kano, S.; Sugino, E.; Hibino, S. J. Chem. Soc. Chem. Commun. 1980, 1241.
5. (b) Kano, S.; Sugino, E.; Shibuya, S.; Hibino, S. J. Org. Chem. 1981, 46, 3856.
6. (c) Takano, S.; Suzuki, Y.; Ogasawara, K. Heterocycles 1981, 16, 1479.
7. (d) Kawasaki, T.; Nonaka, Y.; Sakamoto, M. J. Chem. Soc. Chem. Commun. 1989, 43.
8. (e) Moody, C. J.; Shah, P. J. Chem. Soc. Perkin Trans. 1 1989, 2463.
9. (f) Danheiser, R. L.; Brisbois, R. G.; Kowalczyk, J. J.; Miller, R. F. J. Am. Chem. Soc. 1990, 112, 3093.
10. (g) Kawasaki, T.; Nonaka, Y.; Akahane, M.; Maeda, M.; Sakamoto, M. J. Chem. Soc. Perkin Trans. 1 1993, 1777.
11. (h) Beccalli, E. M.; Marchesini, A.; Pilati, T. J. Chem. Soc. Perkin Trans. 1 1994, 579.
12. (i) Knölker, H.-J.; Baum, E.; Hopfmann, T. Tetrahedron Lett. 1995, 36, 5339.
13. For the isolation of carbazomycins, see: (a) Sakano, K.; Ishimaru, K.; Nakamura, S. J. Antibiotics 1980, 33, 683.
14. (b) Sakano, K.; Nakamura, S. J. Antibiotics 1980, 33, 961.
15. (c) Kaneda, M.; Sakano, K.; Nakamura, S.; Kushi, Y.; Iitaka, Y. Heterocycles 1981, 75, 993.
16. (d) Yamasaki, K.; Kaneda, M.; Watanabe, K.; Ueki, Y.; Ishimaru, K.; Nakamura, S.; Nomi, R.; Yoshida, N.; Nakajima, T. J. Antibiotics 1983, 36, 552.
17. (e) Kondo, S.; Katayama, M.; Marumo, S. J. Antibiotics 1986, 39, 727.
18. (f) Naid, T.; Kitahara, T.; Kaneda, M.; Nakamura, S. J. Antibiotics 1987, 40, 157.
19. (g) Kaneda, M.; Naid, T.; Kitahara, T.; Nakamura, S.; Hirata, T.; Suga, T. J. Antibiotics 1988, 41, 602.
20. For previous syntheses of carbazomycins, see reference 8.
21. For the isolation of carazostatin, see: Kato, S.; Kawai, H.; Kawasaki, T.; Toda, Y.; Urata, T.; Hayakawa, Y. J. Antibiotics 1989, 42, 1879.
22. For previous syntheses of carazostatin, see: (a) Jackson, P. M.; Moody, C. J. Synlett 1990, 521.
23. (b) Jackson, P. M.; Moody, C. J.; Mortimer, R. J. J. Chem. Soc. Perkin Trans. 1 1991, 2941.
24. (c) Shin, K.; Ogasawara, K. Chem. Lett. 1995, 289.
25. (d) Knölker, H.-J.; Hopfmann, T. Synlett 1995, 981.
26. For recent reviews, see: (a) Pindur, U. Chimia, 1990, 44, 406.
27. (b) Bergman, J.; Pelcman, B. Pure Appl. Chem. 1990, 62, 1967.
28. (c) Knölker, H.-J. Synlett 1992, 371.
29. (d) Kawasaki, T.; Sakamoto, M. J. Indian Chem. Soc. 1994, 71, 443.
30. (e) Moody, C. J. Synlett 1994, 681.
31. (f) Knölker, H.-J. in Advances in Nitrogen Heterocycles Moody, C. J. Ed.; JAI Press: Greenwich, CT(USA), 1995, Vol. 1, p. 173.
32. (g) Hibino, S.; Sugino, E. in Advances in Nitrogen Heterocycles Moody, C. J. Ed.; JAI Press: Greenwich, CT(USA), 1995, Vol. 1, p. 205.
33. (a) Schuster, H. F.; Coppola, G. M. "Allenes in Organic Synthesis" Wiley: New York, 1984.
34. (b) Turnbull, P.; Moore, H. W. J. Org. Chem. 1995, 60, 3274 and related references cited therein.
35. 2-Formyl-3-iodoindole (mp 193-194°C, 81%) was prepared from 2-formylindole by the following method: Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1990, 36, 2248.
36. Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 4205.
37. (matrix presented)
38. Rigby, J. H.; Wilson, J. Z. Tetrahedron Lett. 1984, 25, 1429.
39. (a) Ishiyama, T.; Kizaki, H.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1993, 34, 7595.
40. (b) Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201.
41. 3): δ 2.21(3H, s), 4.00(3H, s), 7.18(1H, t, J=7 Hz), 7.25-7.57(7H, m), 7.51(1H, s), 7.60(1H, brs), 8.02(1H, d, J=7 Hz).