A general synthetic approach to the (20s)-camptothecin family of antitumor agents by a regiocontrolled cascade radical cyclization of aryl isonitriles

Chemistry - A European Journal

Volumn 4, Issue 1, 1998, Pages 67-83

  Josien, Hubert ^a   Ko, Sung Bo ^a   Bom, David ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Alkaloids; Antitumor agents; Camptothecins; Cascade reactions; Radical reactions

Indexed keywords

EID: 0031934061     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(199801)4:1<67::AID-CHEM67>3.0.CO;2-F     Document Type: Article

References (108)

1. Leading references: a) M. E. Wall, M. C. Wani, J. Ethnopharmacol. 1996, 51, 239;
2. b) Camptothecin: New Anticancer Agents (Eds.: M. Potmesil, H. Pinedo), CRC, Boca Raton, FL, 1995;
3. c) J. Bonneterre, Bull. Cancer. 1995, 82, 623;
4. d) D. K. Sinha, Drugs 1995, 49, 11.
5. S. J. Froelich-Ammon, N. Osheroff, J. Biol. Chem. 1995, 270, 21429.
6. Recent reviews: a) W. J. Slichenmyer, E. K. Rowinsky, R. C. Donehower, S. H. Kaufmann. J. Natl. Cancer Inst. 1993, 85, 271;
7. for recent advances at the molecular pharmacology level see: b) Y. Pommier, G. Kohlhagen, K. W. Kohn, F. Leteurtre, M. C. Wani, M. E. Wall, Proc. Natl. Acad. Sci. USA 1995, 92, 8861;
8. c) R. Hertzberg, R. W. Busby, M. J. Caranfa, K. G. Holden, R. K. Johnson, S. M. Hecht, W. D. Kingsbury, J. Biol. Chem. 1990, 265, 19287.
9. Due to the poor water-solubility of camptothecin, early clinical tests used its open-ring lactone sodium salt, which was later shown to be poorly active. See ref. [1 b]
10. Leading references: a) K. Lackey, D. D. Sternbach, D. K. Croom, D. L. Emerson, M. G. Evans, P. L. Leitner, M. J. Luzzio, G. McIntyre, A. Vuong, J. Yates, J. M. Besterman, J. Med. Chem. 1996, 39, 713;
11. b) I. Mitsui, E. Kumazawa, Y. Hirota, M. Aonuma, M. Sugimori, S. Ohsuki, K. Uoto, A. Ejima, H. Terasawa, K. Sato, Jpn. J. Cancer Res. 1995, 86, 776;
12. c) T. Yaegashi, S. Sawada, H. Nagata, T. Furuta, T. Yokokura, T. Miyasaka, Chem. Pharm. Bull. 1994, 42, 2518;
13. d) D. E. Uehling, S. S. Nanthakumar, D. Croom, D. L. Emerson, P. L. Leitner, M. J. Luzzio, G. McIntyre, B. Morton, S. Profeta, J. Sisco, D. D. Sternbach, W.-Q. Tong, A. Vuong, J. M. Besterman, J. Med. Chem. 1995, 38, 1106;
14. e) M. Sugimori, A. Ejima, S. Ohsuki, K. Uoto, I. Mitsui, K. Matsumoto, Y. Kawato, M. Yasuoka, K. Sato, H. Tagawa, H. Terasawa, J. Med. Chem. 1994, 37, 3033;
15. f) M. Sugimori, A. Ejima, S. Ohsuki, K. Matsumoto, Y. Kawato, M. Yasuoka, H. Tagawa, H. Terasawa, Heterocycles 1994, 38, 81;
16. g) M. E. Wall, M. C. Wani, A. W. Nicholas, G. Manikumar, C. Tele, L. Moore, A. Truesdale, P. L. Leitner, J. M. Besterman, J. Med. Chem. 1993, 36, 2689;
17. h) L. Snyder, W. Shen, W. G. Bornmann, S. J. Danishefsky, J. Org. Chem. 1994, 59, 7033;
18. i) A. Bedeschi, F. Zarini, W. Cabri, I. Candiani, S. Penco, L. Capolongo, M. Ciomei, M. Farao, M. Grandi, Bioorg. Med. Chem. Lett. 1996, 6, 671;
19. j) R. Zhao, B. Oreski, J. W. Lown, Bioorg. Med. Chem. Lett. 1995, 5, 3063.
20. W. D. Kingsbury, J. C. Boehm, D. R. Jakas, K. G. Holden, S. Hecht, G. Gallagher, M. J. Cavanfa, F. L. MeCabe, L. F. Faucette, R. K. Johnson, R. Hertzberg, J. Med. Chem. 1991, 34, 98.
21. S. Sawada, S. Okajima, R. Aiyama, K.-I. Nokata, T. Furuta, T. Yokokura, E. Sugino, K. Yamaguchi, T. Miyasaka, Chem. Pharm. Bull. 1991, 39, 1446.
22. M. J. Luzzio, J. M. Besterman, D. L. Emerson, M. G. Evans, K. Lackey, P. L. Leitner, G. McIntyre, B. Morton, P. L. Myers, M. Peel, J. M. Sisco, D. D. Sternbach, W.-Q. Tong, A. Truesdale, D. E. Uehling, A. Vuong, J. Yates, J. Med. Chem. 1995, 38, 395.
23. a) M. Fukuda, K. Nishio, F. Kanzawa, H. Ogasawara, T. Ishida, Cancer Res. 1996, 56, 789;
24. b) F. Goldwasser, M. Valenti, R. Torres, K. W. Kohn, Y. Pommier, Clin. Cancer Res. 1996, 2, 687;
25. c) D. S. Wang, Y. Ueno, H. Oyamada, S. Kojima, Biol. Pharm. Bull. 1996, 19, 354.
26. a) D. Subramanian, M. T. Muller, Oncol. Res. 1995, 7, 461;
27. b) S. S. Daoud, M. I. Fetouh, B. C. Giovanella, Anti-Cancer Drugs 1995, 6, 83;
28. c) E. Merisko-Liversidge, P. Sarpotdar, J. Bruno, S. Hajj, L. Wei, N. Peltier, J. Rake, J. M. Shaw, S. Pugh, L. Polin, J. Jones, T. Corbett, E. Cooper, G. G. Liversidge, Pharm. Res. 1996, 13, 272;
29. d) S. M. Sugarman, Y. Y. Zou, K. Wasan, K. Poirot, R. Kumi, Cancer Chemother. Pharmacol. 1996, 37, 531;
30. e) P. Pantazis, Clin. Cancer Res. 1995, 1, 1235.
31. Early approaches see: a) J. C. Cai, C. R. Hutchinson, Chem. Heterocycl. Compd. 1983, 25, 753;
32. b) J. C. Cai, C. R. Hutchinson, The Alkaloids: Chemistry and Pharmacology (Ed.: A. E. Bross), Academic Press, NY, 1983;
33. c) C. R. Hutchinson, Tetrahedron 1981, 37, 1097;
34. d) A. G. Schultz, Chem. Rev. 1973, 73, 385.
35. Recent advances in the enantiomeric series: a) J. M. D. Fortunak, J. Kitteringham, A. R. Mastrocola, M. Mellinger, N. J. Sisti, J. L. Wood, Z.-P. Zhuang, Tetrahedron Lett. 1996, 37, 5683;
36. b) M. A. Ciufolini, F. Roschangar, Angew. Chem. 1996, 108, 1789; Angew. Chem. Int. Ed. Engl. 1996, 35, 1692;
37. b) M. A. Ciufolini, F. Roschangar, Angew. Chem. 1996, 108, 1789; Angew. Chem. Int. Ed. Engl. 1996, 35, 1692;
38. c) D. L. Comins, J. K. Saha, Tetrahedron Lett. 1995, 36, 7995;
39. d) S.-S. Jew, K.-D. Ok, H.-J. Kim, M. G. Kim, J. M. Kim, J. M. Hah, Y.-S. Cho, Tetrahedron: symmetry 1995, 6, 1245;
40. e) D. L. Comins, H. Hong, G. Jianhua, Tetrahedron Lett. 1994, 35, 5331;
41. f) F. G. Fang, S. Xie, M. W. Lowery, J. Org. Chem. 1994, 59, 6142;
42. g) D. L. Comins, M. F. Baevsky, H. Hong, J. Am. Chem. Soc. 1992, 114, 10971. Recent advances in the racemic series:
43. h) A. Ejima, H. Terasawa, M. Sugimori, H. Tagawa, J. Chem. Soc. Perkin Trans. I 1990, 27;
44. i) D. L. Comins, H. Hong, J. K. Saha, G. Jianhua, J. Org. Chem. 1994. 59, 5120;
45. j) A. V. R. Rao, J. S. Yadav. V. Muralikrishna, Tetrahedron Lett. 1994, 35, 3613;
46. k) W. Shen, C. A. Coburn, W. G. Bornmann, S. J. Danishefsky, J. Org. Chem. 1993, 58, 611.
47. See the special issue in Chem. Rev. 1996, 96, Vol 1
48. For example, see: a) P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195;
49. b) B. B. Snider, ibid. 1996, 96, 339;
50. c) B. Fraser-Reid, Acc. Chem. Res. 1996, 29, 57;
51. e) K. K. Wang, Chem. Rev. 1996. 96, 207;
52. d) M. Malacria, ibid. 1996, 96, 289;
53. f) U. Koert, Angew. Chem. 1996, 108, 441; Angew. Chem. Int. Ed. Engl. 1996, 35, 405.
54. f) U. Koert, Angew. Chem. 1996, 108, 441; Angew. Chem. Int. Ed. Engl. 1996, 35, 405.
55. a) D. P. Curran, H. Liu, J. Am. Chem. Soc. 1992, 114, 5863;
56. b) D. P. Curran, J. Chin. Chem. Soc. (Taipei) 1993, 40, 1;
57. c) D. P. Curran, J. Sisko, P. E. Yeske, H. Liu, Pure Appl. Chem. 1993, 65, 1153;
58. d) H. Liu, Dissertation, University of Pittsburgh, 1994;
59. e) D. P. Curran, H. Liu, H. Josien, S.-B. Ko, Tetrahedron 1996, 52, 11385;
60. f) I. Ryu, N. Sonoda, D. P. Curran, Chem. Rev. 1996, 96, 177.
61. D. P. Curran, H. Liu, J. Am. Chem. Soc. 1991, 113, 2127.
62. Only the (20S) isomer shows biological activity: H. Josien, D. Bom, D. P. Curran, Y.-H. Zheng, T.-C. Chou, Bioorg. Med. Chem. Lett. 1997, 7, 3189.
63. D. P. Curran, S.-B. Ko, H. Josien, Angew. Chem. 1995, 108, 2948; Angew. Chem. Int. Ed. Engl. 1995, 34, 2683.
64. D. P. Curran, S.-B. Ko, H. Josien, Angew. Chem. 1995, 108, 2948; Angew. Chem. Int. Ed. Engl. 1995, 34, 2683.
65. a) H. C Kolb, M.S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483;
66. b) K. Morikawa, J. Park, P. G. Anderson, T. Hashiyama, K. B. Sharpless, J. Am. Chem. Soc. 1993, 115, 8463;
67. c) G. A. Crispino, K.-S. Jeong, H. C. Kolb, Z.-M. Wang, D. Xu, K. B. Sharpless, J. Org. Chem. 1993, 58, 3785.
68. D. P. Curran, S.-B. Ko, J. Org. Chem. 1994, 59, 6139.
69. This strategy was prefered to a Davis asymmetric hydroxylation (F. A. Davis, B.-C. Chen, Chem. Rev. 1992, 92, 919) owing to the highly substituted nature of the α-hydroxylactone.
70. D. P. Curran, H. Liu, S.-B. Ko, H. Josien, Tetrahedron Lett. 1995, 36, 8917.
71. J. Cossy, Bull Soc. Chim. Fr. 1994, 131, 344.
72. S. Karady, N. L. Abramson, U. H. Dolling, A. W. Douglas, G. J. McManemin, B. Marcune, J. Am. Chem. Soc. 1995, 117, 5425.
73. Leading references: a) D. Crich, S. Sun, J. Brunckova, J. Org. Chem. 1996, 61, 605;
74. b) D. P. Curran, J. Xu, J. Am. Chem. Soc. 1996, 118, 3142.
75. a) R. J. Mills, N. J. Taylor, V. Snieckus, J. Org. Chem. 1989, 54, 4372;
76. b) W. Wang, V. Snieckus, ibid. 1992, 57, 424.
77. Leading references: a) Silicon in Organic Synthesis (Ed.: E. Colvin), Butterworths, London, 1981;
78. b) A. R. Bassindale, A. R. Taylor, in The Chemistry of Organic Silicon Compounds (Eds.: S. Patai, Z. Rappoport), Wiley, 1989, p. 893.
79. a) L. A. Jacob, B.-L. Chen, D. Stec, Synthesis 1993, 611;
80. b) R. A. Earl, K. P. C. Vollhardt, J. Org. Chem. 1984, 49, 4786;
81. c) F. Effenberger, A. Krebs, ibid. 1984, 49, 4687;
82. d) H. Diaz, J. W. Kelly, Tetrahedron Lett. 1991, 41, 5725;
83. e) S.-S. P. Chou, H. L. Ku,. C. J. Wang, C. Y. Tsai, C. M. Sun, J. Org. Chem. 1989, 54, 860;
84. e) T. H. Chan, K. Koumaglo. Tetrahedron Lett. 1986, 27, 883.
85. B. Fraser-Reid, U. E. Udodong, Z. Wu, H. Ottosson, J. R. Merritt, C. S. Rao, C. Roberts, R. Madsen, Synlett 1992, 927. Lutidine was used instead of collidine.
86. M. Golinski, M. Heine, D. S. Watt, Tetrahedron Lett. 1991, 32, 1553.
87. M. P. Doyle, D. J. DeBruyn, D. A. Kooistra, J. Am. Chem. Soc. 1972, 94, 3659.
88. R. Grigg, V. Sridharan, P. Stevenson, S. Sukirthalingam, T. Worakun, Tetrahedron 1990, 46, 4003.
89. Leading references: a) C. Chatgilialoglu, Chem. Rev. 1995, 95, 1229;
90. b) H. Togo, K. Hayashi, M. Yokoyama, Bull. Chem. Soc. Jpn. 1994, 67, 2522.
91. a) W. P. Weber, G. W. Gokel, Tetrahedron Lett. 1972, 13, 1637;
92. b) R. Appel, R. Kleinstuck, K.-D. Ziehn, Angew. Chem. 1971, 83, 143; Angew. Chem. Int. Ed. Engl. 1971, 10, 132, using carbon tetrabromide in place of carbon tetrachloride.
93. b) R. Appel, R. Kleinstuck, K.-D. Ziehn, Angew. Chem. 1971, 83, 143; Angew. Chem. Int. Ed. Engl. 1971, 10, 132, using carbon tetrabromide in place of carbon tetrachloride.
94. Protective Groups in Organic Synthesis (Eds.: T. H. Greene, P. G. M. Wuts), Wiley, 1991.
95. Recent example: W. Wang, V. Snieckus, J. Org. Chem. 1992, 57, 424.
96. a) D. Habich, F. Effenberger, Synthesis 1979, 841;
97. b) H. Matsumoto, K. Yoshihiro, S. Nagashima, H. Watanabe, Y. Nagai, J. Organomet. Chem. 1977, 128, 409.
98. S. Ram, R. E. Ehrenkauker, Tetrahedron Lett. 1984, 25, 3415.
99. Attempts at N-formylation using HCOOEt resulted in protodesilylation.
100. a) D. L. Comins, J. D. Brown, J. Org. Chem. 1984, 49, 1078;
101. for a review on ortho-metalation see: b) V. Snieckus, Chem. Rev. 1990, 90, 879.
102. L. R. Hill, R. C. Ronald, J. Org. Chem. 1985, 50, 470.
103. 3 failed. See: J. G. Lee, K. H. Kwak, Tetrahedron Lett. 1992, 33, 3165.
104. T. L. Capson, C. D. Poulter, Tetrahedron Lett. 1984, 25, 3515 and references therein.
105. Other attempts at using Hoffman rearrangement on the primary carboxamide derived from 37b proved unsuccessful. For a review of the conditions we tried, see: a) S.-S. Jew, H. G. Park, H.-J. Park, M.-S. Park, Y.-S. Cho, Tetrahedron Lett. 1990, 31, 1559;
106. b) A. Rosenquist, I. Kvarnstrom, S. C. T. Svensson, J. Org. Chem. 1994, 59, 1779.
107. J. E. Baldwin, A. E. Derome, P. D. Riordan, Tetrahedron 1983, 39, 2989.
108. C. Einhorn, J. Einhorn, J. L. Luche, Synlett 1991, 37.