Concise formal syntheses of the Amaryllidaceae Alkaloids (±)-tazettine and (±)-6a-epipretazettine: Construction of the core skeleton via tandem intramolecular oxidative Friedel-crafts/aza-Michael reaction

Chemistry - An Asian Journal

Volumn 8, Issue 2, 2013, Pages 364-368

  Ma, Donghui ^a   Zhao, Changgui ^a   Li, Huilin ^a   Qi, Jing ^a   Zhang, Ling ^a   Xu, Shiyan ^a   Xie, Xingang ^a   She, Xuegong ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

alkaloids; Friedel Crafts reaction; hypervalent compounds; Michael addition; synthesis

Indexed keywords

ALKALOIDS; AMARYLLIDACEAE; CHIRAL CENTERS; CORE STRUCTURE; EFFICIENT SYNTHESIS; FORMAL SYNTHESIS; FRIEDEL-CRAFTS; GRAM SCALE; HYPERVALENT COMPOUNDS; MICHAEL ADDITIONS; P-HYDROXYBENZALDEHYDE;

ADDITION REACTIONS; FRIEDEL-CRAFTS REACTION; METABOLITES; MUSCULOSKELETAL SYSTEM; NITROGEN COMPOUNDS;

SYNTHESIS (CHEMICAL);

6A EPIPRETAZETITINE; 6A-EPIPRETAZETITINE; AMARYLLIDACEAE ALKALOID; HETEROCYCLIC COMPOUND; TAZETTINE;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; LILIACEAE; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMARYLLIDACEAE ALKALOIDS; AZA COMPOUNDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; LILIACEAE; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; STEREOISOMERISM;

MLCS; MLOWN;

EID: 84873807704     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201200964     Document Type: Article

References (58)

1. S. F. Martin, The Alkaloids, Vol. 30 (Ed.:, A. Brossi,), Academic Press, New York, 1987, pp. 251-376
2. O. Hoshino, The Alkaloids, Vol. 51 (Ed.:, A. Brossi,), Academic Press, New York, 1998, pp. 323-424
3. J. R. Lewis, Nat. Prod. Rep. 1998, 15, 107-110
4. Z. Jin, Nat. Prod. Rep. 2005, 22, 111-126.
5. W. C. Wildman, C. J. Kaufman, J. Am. Chem. Soc. 1954, 76, 5815-5816; isolations of pretazettine and 6a-epipretazettine
6. W. C. Wildman, D. T. Bailey, J. Org. Chem. 1968, 33, 3749-3753
7. W. C. Wildman, D. T. Bailey, J. Am. Chem. Soc. 1969, 91, 150-157.
8. E. Furusawa, H. Irie, D. Combs, W. C. Wildman, Chemotherapy 1980, 26, 36-45
9. T. S. Papas, L. Sandhaus, M. A. Chirigos, E. Furusawa, Biochem. Biophys. Res. Commun. 1973, 52, 88-92
10. N. Suzuki, S. Tani, S. Furusawa, E. Furusawa, Proc. Soc. Exp. Biol. Med. 1974, 145, 771-777
11. E. Furusawa, N. Suzuki, S. Furusawa, J. Y. B. Lee, Proc. Soc. Exp. Biol. Med. 1975, 149, 771-778
12. E. Furusawa, S. Furusawa, J. Y. B. Lee, S. Patanavanich, Proc. Soc. Exp. Biol. Med. 1976, 152, 186-191
13. E. Furusawa, S. Furusawa, J. Y. B. Lee, S. Patanavanich, Chemotherapy 1978, 24, 259-266
14. E. Furusawa, R. H. Lockwood, S. Furusawa, M. K. M. Lum, J. Y. B. Lee, Chemotherapy 1979, 25, 308-315
15. E. Furusawa, H. Irie, D. Combs, W. C. Wildman, Chemotherapy 1980, 26, 36-45
16. E. Furusawa, M. K. M. Lum, S. Furusawa, Chemotherapy 1981, 27, 277-286
17. E. Furusawa, S. Furusawa, L. Sokugawa, Chemotherapy 1983, 29, 294-302
18. E. Furusawa, S. Furusawa, Onocology 1988, 45, 180-186.
19. J. B. Hendrickson, T. L. Bogard, M. E. Fisch, J. Am. Chem. Soc. 1970, 92, 5538-5539
20. Y. Tsuda, K. Isobe, J. Chem. Soc. D, Chem. Commun. 1971, 1555-1556
21. Y. Tsuda, A. Ukai, K. Isobe, Tetrahedron Lett. 1972, 13, 3153-3156
22. J. B. Hendrickson, T. L. Bogard, M. E. Fisch, S. Grossert, N. Yoshimura, J. Am. Chem. Soc. 1974, 96, 7781-7789
23. S. Danishefsky, J. Morris, G. Mullen, R. Gammill, J. Am. Chem. Soc. 1980, 102, 2838-2840
24. S. Danishefsky, J. Morris, G. Mullen, R. Gammill, J. Am. Chem. Soc. 1982, 104, 7591-7599
25. J. D. White, W. K. M. Chong, K. Thirring, J. Org. Chem. 1983, 48, 2300-2302
26. S. F. Martin, S. K. Davidsen, J. Am. Chem. Soc. 1984, 106, 6431-6433
27. S. F. Martin, S. K. Davidsen, T. A. Puckette, J. Org. Chem. 1987, 52, 1962-1972
28. L. E. Overman, H. Wild, Tetrahedron Lett. 1989, 30, 647-650
29. H. Ishibashi, H. Nakatani, S. Iwami, T. Sato, N. Nakamura, M. Ikeda, J. Chem. Soc. Chem. Commun. 1989, 1767-1769
30. M. M. Abelman, L. E. Overman, V. D. Tran, J. Am. Chem. Soc. 1990, 112, 6959-6964
31. S. W. Baldwin, J. Aubé, A. T. McPhail, J. Org. Chem. 1991, 56, 6546-6550
32. H. Ishibashi, N. Uemura, H. Nakatani, M. Okazaki, T. Sato, N. Nakamumra, M. Ikeda, J. Org. Chem. 1993, 58, 2360-2368
33. W. H. Pearson, M. J. Postich, J. Org. Chem. 1994, 59, 5662-5671
34. J. H. Rigby, A. Cavezza, M. J. Heeg, J. Am. Chem. Soc. 1998, 120, 3664-3670
35. T. Nishimata, M. Mori, J. Org. Chem. 1998, 63, 7586-7587
36. S. W. Baldwin, J. S. Debenham, Org. Lett. 2000, 2, 99-102
37. T. Nishimata, Y. Sato, M. Mori, J. Org. Chem. 2004, 69, 1837-1843
38. F.-M. Zhang, Y.-Q. Tu, J.-D. Liu, X.-H. Fan, L. Shi, X.-D. Hu, S.-H. Wang, Y.-Q. Zhang, Tetrahedron 2006, 62, 9446-9455
39. A. L. Lehmann, A. C. Willis, M. G. Banwell, Aust. J. Chem. 2010, 63, 1665-1678
40. G. R. Ebrahimian, X. M. Jourdin, P. L. Fuchs, Org. Lett. 2012, 14, 2630-2633.
41. K. C. Guérard, C. Sabot, L. Racicot, S. Canesi, J. Org. Chem. 2009, 74, 2039-2045.
42. W. Kurosawa, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2003, 125, 8112-8113.
43. Q. Cheng, T. Oritani, T. Horiguchi, Q.-W. Shi, Eur. J. Org. Chem. 1999, 2689-2693.
44. R. S. Ward, D. D. Hughes, Tetrahedron 2001, 57, 5633-5639
45. N. T. Vo, R. D. M. Pace, F. O'Hara, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 404-405
46. C.-G. Zhao, H.-J. Zheng, P. Jing, B.-W. Fang, X.-G. Xie, X.-G. She, Org. Lett. 2012, 14, 2293-2295; Reviews
47. L. Pouységu, D. Deffieux, S. Quideau, Tetrahedron 2010, 66, 2235-2261
48. S. P. Roche, J. A. Porco, Jr., Angew. Chem. 2011, 123, 4154-4179
49. Angew. Chem. Int. Ed. 2011, 50, 4068-4093.
50. T. Dohi, T. Uchiyama, D. Yamashita, N. Washimi, Y. Kita, Tetrahedron Lett. 2011, 52, 2212-2215
51. T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, Y. Kita, Angew. Chem. 2008, 120, 3847-3850
52. Angew. Chem. Int. Ed. 2008, 47, 3787-3790
53. T. Dohi, Y. Kita, Chem. Commun. 2009, 2073-2085
54. H. Tohma, Y. Harayama, M. Hashizume, M. Iwata, Y. Kiyono, M. Egi, Y. Kita, J. Am. Chem. Soc. 2003, 125, 11235-11240
55. T. Dohi, Y. Minamitsuji, A. Maruyama, S. Hirose, Y. Kita, Org. Lett. 2008, 10, 3559-3562.
56. N. W. Alcock, T. C. Waddington, J. Chem. Soc. 1963, 4103
57. J. Gallos, A. Varvoglis, N. W. Alcock, J. Chem. Soc. Perkin Trans. 1 1985, 757-763.
58. J. G. Pierce, D. Kasi, M. Fushimi, A. Cuzzupe, P. Wipf, J. Org. Chem. 2008, 73, 7807-7810.