Nickel-catalyzed preparation of bicyclic heterocycles: Total synthesis of (+)-allopumiliotoxin 267A, (+)-allopumiliotoxin 339A, and (+)-allopumiliotoxin 339B

Journal of the American Chemical Society

Volumn 122, Issue 29, 2000, Pages 6950-6954

  Tang, Xiao Qing ^a   Montgomery, John ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOPUMILIOTOXIN; NICKEL; PYRROLIZIDINE; TOXIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; FROG; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034718064     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001440t     Document Type: Article

References (48)

1. (a) Daly, J. W.; Garraffo, H. M.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1999; Vol. 13, Chapter 1.
2. (b) Tokuyama, T.; Daly, J. W.; Highet, R. J. Tetrahedron 1984,40, 1183.
3. Franklin, A.; Overman, L. E. Chem. Rev. 1996, 96, 505.
4. (a) Goldstein, S. W.; Overman, L. E.; Rabinowitz, M. H. J. Org. Chem. 1992, 57, 1179.
5. (b) Overman, L. E.; Robinson, L. A.; Zablocki, J. J. Am. Chem. Soc. 1992, 114, 368.
6. Caderas, C; Lett, R.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 7/5, 9073 and references therein.
7. Trost, B. M.; Scanlan, T. S. J. Am. Chem. Soc. 1989, 111, 4988.
8. (a) Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644.
9. (b) Takai, K.; Tagashira, M.; Kuroda. T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048.
10. (a) Aoyagi, S.; Wang, T.; Kibayashi, C. J. Am. Client. Soc. 1993, 115, 11393.
11. (b) Aoyagi, S.; Wang, T.; Kibayashi, C. J. Am. Chem. Soc. 1992, 114, 10653.
12. Okamoto, S.; hvakubo, M.; Kobayashi, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 6984.
13. Portions of this work have previously been communicated: Tang, X. Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098.
14. (a) For an extensive review, see: Ojima, I.; Tzamarioudaki, M.; Li, Z. Y.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
15. (b) For an early example of this reaction class, see: Trost, B. M.; Rise, F. J.'Am. Chem. Soc. 1987, 109, 3161.
16. Hewlett, D. F.; Whitby, R. J. J. Chem. Soc., Client. Commun. 1990, 1684.
17. (a) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995,117, 6785-6786.
18. (b) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 775,3182-3191.
19. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995,117, 6787-6788.
20. (a) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
21. (b) Sato, Y.; Takimoto, M.; Mori, M. Tetrahedron Lett. 1996, 37, 887.
22. Takimoto, M.; Hiraga, Y.; Sato, Y.; Mori, M. Tetrahedron Lett. 1998, 39, 4543.
23. (a) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 720, 4033.
24. (b) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y.Angew. Chem., Int. Ed. 1999, 38, 397.
25. (a) Sato, Y.; Saito, N.; Mori, M. Tetrahedron Lett. 1997,38, 3931.
26. (b) Sato, Y.; Saito, N.; Mori, M. Tetrahedron 1998,54. 1153.
27. Sato, Y.; Takimoto, H.; Mon, M. Synlett 1997, 6, 734.
28. (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 779, 9065-9066.
29. (b) Montgomery, J. Ace. Chem. Res. In press.
30. For other transition metal-catalyzed cyclizations involving hydrosilanes, see: (a) Ojima, I.; Zhu, J. W.; Vidai, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 720, 6690.
31. (b) Trost, B. M.; Rise, F. J. Am. Chem. Soc. 1987, 709,3161-3163.
32. Tamao, K.; Kobayashi, K.; Ito, Y. J. Ain. Chem. Soc. 1989, 111, 6478.
33. Takacs, J.; Chandramouli, S. Orgauometallics 1990, 9, 2877.
34. (e) Widenhoefer, R. A.; DeCarli, M. A. J. Ain. Chem. Soc. 1998, 720, 3805.
35. (0 Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 777,4415.
36. (a) Michael, J. P. Nat. Prod. Rep. 1999, 70, 675.
37. (b) Kinghom, A. D.; Balandrin, M. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1984; Vol. 2, Chapter 3.
38. Herbert, R. B. In Alkaloids: Chemical and Biological Perspectives', Pelletier, S. W., Ed.; Wiley: New York, 1985; Vol. 3, Chapter 6.
39. Pearson, W. H.; Suga, H. J. Org. Chem. 1998, 63, 9910.
40. (a) Liddell, J. R. Nat. Prod. Rep. 1999, 76,499.
41. (b) Hartmann, T.; Witte, L. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1995; Vol. 9, Chapter 4.
42. Broggini, G.; Zecchi, G. Synthesis 1999, 6,905.t
43. Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1998, 720, 1757.
44. Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1987; Vol. 5, Chapter 1.
45. Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554.
46. For examples of late-metal-catalyzed a-bond metatheses, see ref 17e and: (a) LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 779, 9066.
47. (b) Hartwig, 1. F.; Bhandari, S.; Rablen, P. R. J. Am. Chem. Soc. 1994, 116, 1839.
48. Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226.