From Aziridines to Oxazolines and Thiazolines: The Heterocyclic Route to Thiangazole

Synlett

Volumn 1997, Issue 1, 1997, Pages 1-10

  Wipf, Peter ^a   Venkatraman, Srikanth ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010372191     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-681     Document Type: Article

References (94)

1. a) Carmeli, S.; Moore, R. E.; Patterson, G. M. L.; Corbett, T. H.; Valeriote, F. A. J. Am. Chem. Soc. 1990, 112, 8195.
2. b) Carmeli, S.; Paik, S.; Moore, R. E.; Patterson, G.; Yoshida, W. Y. Tetrahedron Lett. 1993, 34, 6681.
3. (c) Fukuyama, T.; Xu, L. H. J. Am. Chem. Soc. 1993, 115, 8449.
4. a) Carmeli, S.; Moore, R. E.; Patterson, G. M. L. Tetrahedron Lett. 1991, 32, 2593.
5. b) Parsons, R. L.; Heathcock, C. H. Tetrahedron Letters 1994, 35, 1379.
6. c) Pattenden, G.; Thom, S. Synlett 1992, 533.
7. d) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1992, 57, 5566.
8. e) Pattenden, G.; Thom, S. M. J. Chem. Soc. Perkin Trans. 1 1993, 21, 1629.
9. f) Parsons, R. L.; Heathcock, C. H. Tetrahedron Lett. 1994, 35, 1383.
10. g) Boyce, R. J.; Pattenden, G. Synlett 1994, 587.
11. h) Boyce, R. J.; Pattenden, G. Tetrahedron 1995, 51, 7313.
12. Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 846.
13. a) Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M. J. Am. Chem. Soc. 1986, 108, 847.
14. b) Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M.; Noguchi, H.; Sankawa, U. J. Org. Chem. 1989, 54, 1360.
15. Kernan, M. R.; Molinski, T. F.; Faulkner, D. J. J. Org. Chem. 1988, 53, 5014.
16. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hashimoto, K. Tetrahedron Lett. 1989, 30, 2809.
17. For a survey of other thiazoline and oxazoline-containing marine natural products, see: a) Wipf, P. Chem. Rev. 1995, 95, 2115. b) Davidson, B. S. Chem. Rev. 1993, 93, 1771. c) Faulkner, D. J. Nat. Prod Rep. 1995, 12, 233.
18. For a survey of other thiazoline and oxazoline-containing marine natural products, see: a) Wipf, P. Chem. Rev. 1995, 95, 2115. b) Davidson, B. S. Chem. Rev. 1993, 93, 1771. c) Faulkner, D. J. Nat. Prod Rep. 1995, 12, 233.
19. For a survey of other thiazoline and oxazoline-containing marine natural products, see: a) Wipf, P. Chem. Rev. 1995, 95, 2115. b) Davidson, B. S. Chem. Rev. 1993, 93, 1771. c) Faulkner, D. J. Nat. Prod Rep. 1995, 12, 233.
20. Umezawa, H. Antibiotics 1975, 3, 21.
21. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303.
22. Higa, T.; Tanaka, J.; Kitamura, A.; Koyama, T.; Takahashi, M.; Uchida, T. Pure Appl. Chem. 1994, 66, 2227.
23. (a) Bayer, A.; Freund, S.; Nicholson, G.; Jung, G. Angew. Chem. Int. Ed. Engl. 1993, 32, 1336.
24. (b) Yorgey, P.; Lee, J.; Koerdel, J.; Vivas, E.; Warner, P.; Jebaratnam, D.; Kolter, R. Proc. Natl. Acad. Sci. USA 1994, 91, 4519.
25. Nagatsu, A.; Kajitani, H.; Sakakibara, J. Tetrahedron Lett. 1995, 36, 4097.
26. Trowitzsch, W.; Höfle, G.; Sheldrick, W. S. Tetrahedron Lett. 1981, 22, 3829.
27. Jansen, R.; Kunze, B.; Reichenbach, H.; Jurkiewicz, E.; Hunsmann, G.; Höfle, G. Liebigs Ann. Chem. 1992, 357.
28. Höfle, G.; Bedorf, N.; Forche, E.; Gerth, K.; Irschik, H.; Jansen, R.; Kunze, B.; Reichenbach, H.; Sasse, F. PCT Int. Appl. WO 92 11,258; CA 117:226295w.
29. (a) Hunsmann, G.; Jurkiewicz, E.; Reichenbach, H.; Forche, E.; Gerth, K.; Irschik, H.; Kunze, B.; Sasse, F.; Höfle, G. PCT Int. Appl. WO 92 11,008; CA 118:52420m. (b)
30. (a) Boyce, R. J.; Mulqueen, G. C.; Pattenden, G. Tetrahedron Letters 1994, 35, 5705.
31. (b) Boyce, R. J.; Mulqueen, G. C.; Pattenden, G. Tetrahedron 1995, 51, 7321.
32. Ehrler, J.; Farooq, S. Synlett 1994, 9, 702.
33. Parsons, R. L.; Heathcock, C. H. J. Org. Chem. 1994, 59, 4733.
34. Jansen, R.; Schomburg, D.; Höfle, G. Liebigs Ann. Chem. 1993, 701.
35. Kunze, B.; Jansen, R.; Pridzun, L.; Jurkiewicz, E.; Hunsmann, G.; Höfle, G.; Reichenbach, H. J. Antibiot. 1993, 46, 1752.
36. The stereochemistry shown was chosen in analogy to the kabiramide B stereochemistry, which is related, but not identical, to scytophycin configurations: (a) Matsunaga, S.; Fusetani, N. ORGN 191, 1995 Int. Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, USA, Dec. 17-22, 1995. (b) Pattenden, G. J. Heterocycl. Chem. 1992, 29, 607. It is important to note that ulapualide, halichondramide, and mycalolide stereochemistry remains to be established independently.
37. The stereochemistry shown was chosen in analogy to the kabiramide B stereochemistry, which is related, but not identical, to scytophycin configurations: (a) Matsunaga, S.; Fusetani, N. ORGN 191, 1995 Int. Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, USA, Dec. 17-22, 1995. (b) Pattenden, G. J. Heterocycl. Chem. 1992, 29, 607. It is important to note that ulapualide, halichondramide, and mycalolide stereochemistry remains to be established independently.
38. (a) Wipf, P.; Kim, H. Y. Tetrahedron Lett 1992, 33, 4275.
39. (b) Wipf, P.; Kim, Y. Tetrahedron Lett. 1992, 33, 5477.
40. (c) Wipf, P.; Miller, C. P. J. Am. Chem. Soc. 1992, 114, 10975.
41. (d) Wipf, P.; Kim, Y. J. Org. Chem. 1993, 58, 1649.
42. (e) Wipf, P.; Kim, H. Y. J. Org. Chem. 1993, 58, 5592.
43. (f) Wipf, P.; Kim, Y.; Fritch, P. C. J. Org. Chem. 1993, 58, 7195.
44. (g) Wipf, P.; Kim, Y. J. Org. Chem. 1994, 59, 3518.
45. (h) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558.
46. (i) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106.
47. (a) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 907.
48. (b) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267.
49. Review: Koert, U. Nachr. Chem. Tech. Lab. 1995, 43, 347.
50. (a) Pattenden, G.; Thom, S. M. J. Chem. Soc. Perkin Trans. 1 1993, 21, 1629.
51. (b) Pattenden, G.; Thom, S. M.; Jones, M. F. Tetrahedron 1993, 49, 2131.
52. Coste, J.; LeNguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205.
53. Meyers, A. I.; Tavares, F. Tetrahedron Lett. 1994, 35, 2481.
54. Karady, S; Amato, J. S.; Weinstock, L. M. Tetrahedron Lett. 1984, 25, 4337.
55. PyBroP = Bromotripyrrolidinophosphonium hexafluorophosphate: Coste, J.; Frerot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437.
56. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
57. Evans, D. L.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L.; Meyers, A. I. J. Org. Chem. 1979, 44, 497.
58. Barrish, J. C.; Singh, J.; Spergel, S. H.; Han, W.-C.; Kissick, T. P.; Kronenthal, D. R.; Mueller, R. H. J. Org. Chem. 1993, 58, 4494.
59. Robinson, R. J. Chem. Soc. 1909, 95, 2167.
60. For a review, see: Turchi, I. J. In The Chemistry of Heterocyclic Compounds, 45; Wiley: New York, 1986; pp 1-342.
61. Castro, B. R. Org. React. 1983, 29, 1.
62. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604.
63. Huisgen, R.; Seidel, M. Chem. Ber. 1961, 94, 2509. See also: Williams, E. L. Tetrahedron Lett. 1992, 33, 1033.
64. Huisgen, R.; Seidel, M. Chem. Ber. 1961, 94, 2509. See also: Williams, E. L. Tetrahedron Lett. 1992, 33, 1033.
65. See, for example: (a) Seebach, D.; Aebi, J. D.; Gander-Coquez, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (b) Groth, U.; Chiang, Y.; Schöllkopf, U. Liebigs Ann. Chem. 1982, 1756. (c) Moon, S.-H.; Ohfune, Y. J. Am. Chem. Soc. 1994, 116, 7405. (d) Williams, R. M.; Im, M.-N. J. Am. Chem. Soc. 1991, 113, 9276.
66. See, for example: (a) Seebach, D.; Aebi, J. D.; Gander-Coquez, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (b) Groth, U.; Chiang, Y.; Schöllkopf, U. Liebigs Ann. Chem. 1982, 1756. (c) Moon, S.-H.; Ohfune, Y. J. Am. Chem. Soc. 1994, 116, 7405. (d) Williams, R. M.; Im, M.-N. J. Am. Chem. Soc. 1991, 113, 9276.
67. See, for example: (a) Seebach, D.; Aebi, J. D.; Gander-Coquez, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (b) Groth, U.; Chiang, Y.; Schöllkopf, U. Liebigs Ann. Chem. 1982, 1756. (c) Moon, S.-H.; Ohfune, Y. J. Am. Chem. Soc. 1994, 116, 7405. (d) Williams, R. M.; Im, M.-N. J. Am. Chem. Soc. 1991, 113, 9276.
68. See, for example: (a) Seebach, D.; Aebi, J. D.; Gander-Coquez, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (b) Groth, U.; Chiang, Y.; Schöllkopf, U. Liebigs Ann. Chem. 1982, 1756. (c) Moon, S.-H.; Ohfune, Y. J. Am. Chem. Soc. 1994, 116, 7405. (d) Williams, R. M.; Im, M.-N. J. Am. Chem. Soc. 1991, 113, 9276.
69. Wipf, P.; Venkatraman, S.; Miller, C. P. Tetrahedron Lett. 1995, 36, 3639.
70. (a) McEwen, W. E.; Conrad, W. E.; VanderWerf, C. A. J. Am. Chem. Soc. 1952, 74, 1168.
71. (b) Ittah, Y.; Sasson, Y.; Shahak, I.; Tsaroom, S.; Blum, J. J. Org. Chem. 1978, 43, 4271.
72. (c) Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 1.
73. Atherton, E.; Sheppard, R. C.; Wade, J. D. J. Chem. Soc. Chem. Commun. 1983, 1060.
74. Miller, C. P.; PhD Thesis, University of Pittsburgh, 1994.
75. (a) Tiers, G. V. D. US patent 3,141,898 (1964) [Chem Abs. 61, P9527c].
76. (b) Weinreb, S. M.; Demko, D. M.; Lessen, T. A.; Demers, J. P. Tetrahedron Lett. 1986, 27, 2099.
77. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 1575.
78. (a) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 907.
79. (b) Burgess, E. M.; Penton, H. R.; Taylor, E. A.; Williams, W. M. Org. Syn. 1973, 53, 1857.
80. (a) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267.
81. (b) Galeotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807.
82. See, for example, ref. 2d and: (a) Crooks, H. M. Chem. Penicillin 1949, 455. (b) Nys, J.; Libeer, J. Bull. Soc. Chim. Belg. 1956, 65, 403. (c) Minster, D. K.; Jordis, U.; Evans, D. L.; Hecht, S. M. J. Org. Chem. 1978, 43, 1624.
83. See, for example, ref. 2d and: (a) Crooks, H. M. Chem. Penicillin 1949, 455. (b) Nys, J.; Libeer, J. Bull. Soc. Chim. Belg. 1956, 65, 403. (c) Minster, D. K.; Jordis, U.; Evans, D. L.; Hecht, S. M. J. Org. Chem. 1978, 43, 1624.
84. See, for example, ref. 2d and: (a) Crooks, H. M. Chem. Penicillin 1949, 455. (b) Nys, J.; Libeer, J. Bull. Soc. Chim. Belg. 1956, 65, 403. (c) Minster, D. K.; Jordis, U.; Evans, D. L.; Hecht, S. M. J. Org. Chem. 1978, 43, 1624.
85. Goldberg, A. A.; Kelly, W. J. Chem. Soc. 1948, 1919.
86. Fry, E. M. J. Org. Chem. 1950, 15, 802.
87. (a) Brittain, J.; Gareau, Y. Tetrahedron Lett. 1993, 34, 3363.
88. (b) Shiao, M.-J.; Lai, L.-L.; Ku, W.-S.; Lin, P.-Y.; Hwu, J. R. J. Org. Chem. 1993, 58, 4742.
89. Wipf, P.; Venkatraman, S.; Fritch, P. C.; Miller, C. P. Tetrahedron Lett. 1995, 36, 6395.
90. Wipf, P.; Fritch, P. C. Tetrahedron Lett. 1994, 35, 5397.
91. Barton, D. H. R.; Motherwell, W. B.; Wozniak, J.; Zard, S. Z. J. Chem. Soc. Perkin Trans 1 1985, 1865.
92. We would like to thank Drs. S. Thaisrivongs and K.-T. Chong from Upjohn Co. and Dr. S. R. Turk from NIAID for providing us with the evaluation of anti-HIV-1 efficacy and cytotoxicity.
93. We thank Prof. John S. Lazo, Department of Pharmacology, University of Pittsburgh, for performing the cell assays.
94. Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599.