Synthesis of cytostatic tetradecacyclic pyrazines and a novel reduction-oxidation sequence for spiroketal opening in sapogenins

Helvetica Chimica Acta

Volumn 83, Issue 8, 2000, Pages 1854-1880

  Bäsler, Siegfried ^a   Brunck, Annette ^b   Jautelat, Rolf ^a   Winterfeldt, Ekkehard ^b  

^a BAYER PHARMA AG   (Germany)

^b LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CEPHALOSTATIN 1; CEPHALOSTATIN 2; CISPLATIN; DOXORUBICIN; FLUOROURACIL; PYRAZINE DERIVATIVE; SAPOGENIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CYTOSTASIS; DRUG EFFECT; DRUG SYNTHESIS; HUMAN; HUMAN CELL; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033844267     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20000809)83:8<1854::AID-HLCA1854>3.0.CO;2-4     Document Type: Article

References (77)

1. a) G. R. Pettit, M. Inoue, Y. Kamano, D. L. Herald, C. Arm, C. Dufresne, N. D. Christie, J. M. Schmidt, D. L. Doubek, T. S. Krupa, J. Am. Chem. Soc. 1988, 110, 2006;
2. b) G. R. Pettit, M. R. Boyd, J.-P. Xu, N. Christie, J. M. Schmidt, D. L. Doubek, J. Nat. Prod. 1994, 57, 52;
3. c) G. R. Pettit, R. Tan, J.-P. Xu, Y. Ichihara, M. D. Williams, M. R. Boyd, J. Nat. Prod. 1998, 61, 955; and ref. cit. therein.
4. N. Fusetani, S. Fukuzawa, S. Matsunaga, J. Org. Chem. 1994, 59, 6164;
5. N. Fusetani, S. Fukuzawa, S. Matsunaga, J. Org. Chem. 1997, 62, 4484.
6. National Cancer Institute (NCI), http://epnws1.ncicrf.gov:2345/dis3d/drug/main.html
7. B. K. Carté, BioScience 1996, 46, 271.
8. A. Ganesan, Angew. Chem. 1996, 108, 667;
9. Angew. Chem., Int. Ed. 1996, 35, 611.
10. C. H. Heathcock, S. C. Smith, J. Org. Chem. 1994, 59, 6828.
11. a) P. L. Fuchs, J. U. Jeong, S. C. Sutton, S. Kim, J. Am. Chem. Soc. 1995, 117, 10157;
12. b) P. L. Fuchs, T. G. LaCour, C. Guo, S. Bhandaru, M. R. Boyd, J. Am. Chem. Soc. 1998, 120, 692;
13. c) P. L. Fuchs, T. G. LaCour, C. Guo, Bioorg. Med. Chem. Lett. 1999, 9, 419; and ref. cit. therein.
14. M. Drögemüller, R. Jautelat, E. Winterfeldt, Angew. Chem. 1996, 108, 1669;
15. Angew. Chem., Int. Ed. 1996, 35, 1572;
16. M. Drögemüller, T. Flessner, R. Jautelat, U. Scholz, E. Winterfeldt, Eur. J. Org. Chem. 1998, 2811.
17. a) A. Kramer, U. Ullmann, E. Winterfeldt, J. Chem. Soc., Perkin Trans. 1 1993, 2865;
18. b) R. Jautelat, A. Müller-Fahrnow, E. Winterfeldt, J. Prakt. Chem. 1996, 338, 695.
19. M. R. Boyd, K. D. Paull, L. R. Rubinstein, in 'Antitumor Drug Discovery and Development', Eds. F. A. Valeriote, T. Corbett, and L. Baker, Kluwer Academic Press, Amsterdam, 1992, p. 11.
20. M. R. Boyd, K. D. Paull, Drug Dev. Res. 1995, 34, 91.
21. G. Majetich, K. Wheless, Tetrahedron 1995, 51, 7095.
22. a) J. Kalvoda, K. Heusler, Synthesis 1971, 501;
23. b) J. Kalvoda, K. Heusler, in 'Organic Reactions in Steroid Chemistry', Vol. 2, Eds. J. Fried and J. A. Edwards, Van Nostrand Reinhold Company, New York, 1971, p. 239.
24. a) D. H. R. Barton, J. Allen, R. B. Boar, J. F. McGhie, J. Chem. Soc., Perkin Trans. 1 1973, 2402;
25. b) R. B. Boar, D. B. Copsey, J. Chem. Soc., Perkin Trans. 1 1979, 563.
26. P. Bladon, W. McMeekin, I. A. Williams, J. Chem. Soc. 1963, 5727.
27. A. Weichert, H. M. R. Hoffmann, J. Chem. Soc., Perkin Trans. 1 1990, 2154.
28. a) E. J. Corey, J. W. Suggs, Tetrahedron Lett. 1975, 16, 2647;
29. b) R. Jautelat, A. Müller-Fahrnow, E. Winterfeldt, Chem. Eur. J. 1999, 5, 1226.
30. T. K. Jones, R. A. Reamer, R. Desmond, S. G. Mills, J. Am. Chem. Soc. 1990, 112, 2998;
31. P. Kocienski, M. Stocks, D. Donald, M. Perry, Synlett 1990, 38.
32. H. C. Brown, A. K. Mandal, S. U. Kulkarni, J. Org. Chem. 1977, 42, 1392.
33. D. H. R. Barton, R. H. Hesse, M. M. Pechet, L. C. Smith, J. Chem. Soc., Perkin Trans. 1 1979, 1159;
34. K. Kinbara, H. Takezaki, A. Kai, K. Saigo, Chem. Lett. 1996, 217.
35. M. Node, T. Kajimoto, N. Ito, J. Tamada, E. Fujita, K. Fuji, J. Chem. Soc., Chem. Commun. 1986, 1164;
36. P. Brun, B. Waegell, Tetrahedron 1970, 52, 1137.
37. a) G. A. Olah, S. C. Narang, B. G. B. Gupta, R. Malhotra, J. Org. Chem. 1979, 44, 1247;
38. R. Amouroux, P. Mimero, C. Saluzzo, Tetrahedron Lett. 1994, 35, 1553;
39. b) K. B. Sharpless, P. H. J. Carlsen, T. Katsuki, V. S. Martin, J. Org. Chem. 1981, 46, 3936;
40. H. B. Henbest, B. Nicholls, J. Chem. Soc. 1959, 221.
41. P. Kraft, W. Tochtermann, Tetrahedron 1995, 51, 10875;
42. S. Hillers, A. Niklaus, O. Reiser, J. Org. Chem. 1993, 58, 3169;
43. D. Meng, E. J. Sorensen, P. Bertinato, S. Danishefsky, J. Org. Chem. 1996, 61, 7998.
44. W. C. Still, J. Am. Chem. Soc. 1978, 100, 1481;
45. P. Wipf, Y. Kim, P. C. Fritch, J. Org. Chem. 1993, 58, 7195;
46. M. Göres, E. Winterfeldt, J. Chem. Soc., Perkin Trans. 1 1994, 3525.
47. V. Vovsi, Russ. Chem. Rev. 1969, 38, 487.
48. R. N. Lacy, Adv. Org. Chem. 1960, 2, 213.
49. Y. Tamura, T. Yakura, J. Haruta, Y. Kita, J. Org. Chem. 1987, 52, 3927.
50. M. Azadi-Ardakani, R. Hayes, T. W. Wallace, Tetrahedron 1990, 46, 6851;
51. S. Dhanalekshmi, K. K. Balasubramanian, C. S. Venkatachalam, Tetrahedron Lett. 1991, 32, 7591.
52. U. Eder (Schering AG, Berlin, Germany), personal communication, 1997.
53. R. C. Ellis, W. B. Whalley, K. Ball, J. Chem. Soc., Perkin Trans. 1 1976, 1377.
54. G. Stork, T. Takahashi, J. Am. Chem. Soc. 1977, 99, 1275.
55. R. Criegee, L. Kraft, B. Rank, Liebigs Ann. Chem. 1933, 507, 159.
56. J. E. Baldwin, C. Najera, M. Yus, J. Chem. Soc., Chem. Commun. 1985, 126.
57. R. Tschesche, W. Führer, Chem. Ber. 1978, 111, 3300.
58. U. Scholz, Ph.D. Thesis, University of Hannover, 1999;
59. U. Scholz, E. Winterfeldt, in preparation.
60. E. Winterfeldt, C. Borm, F. Nerenz, Adv. Asymm. Synth. 1997, 2, 1.
61. R. Appel, M. Halstenberg, Organophosphorus Reagents in Organic Synthesis', Academic Press, New York, 1979;
62. J.-D. Arndt, Ph.D. Thesis, University of Hannover 1998.
63. T. G. LaCour, Z. Tong, P. L. Fuchs, Org. Lett. 1999, 1, 1815.
64. D. A. Horne, Tetrahedron Lett. 1978, 19, 1357;
65. B. M. Trost, I. Fleming, 'Comprehensive Organic Synthesis', Vol. 8, Pergamon Press, Oxford, 1991, p. 218.
66. a) M. J. Thompson, I. Scheer, E. Mosettig, J. Am. Chem. Soc. 1959, 81, 5225;
67. M. A. Iglesias Artega, R. Perez Gil, V. Leliebre Lara, C. S. Perez Martinez, F. Coll Manchado, A. Rosado Perez, L. Pozo Rios, Synth. Commun. 1998, 28, 1381;
68. b) A. H. Albert, G. R. Pettit, P. Brown, J. Org. Chem. 1973, 38, 2197.
69. S. Wolff, M. E. Huecas, W. C. Agosta, J. Org. Chem. 1982, 47, 4358;
70. Y. Q. Tu, C. J. Moore, W. Kitching, Tetrahedron: Asymmetry 1995, 6, 397.
71. M. Iwasaki, Tetrahedron 1967, 23, 2145.
72. L. Fieser, M. Fieser, 'Steroide', Verlag Chemie, Weinheim, 1961.
73. G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467.
74. G. M. Sheldrick, T. R. Schneider, Methods Enzymol. 1997, 227, 319.
75. J. S. Rollet, in 'Crystallographic Computing', Eds. F. R. Ahmed, S. R. Hall, and C. P. Huber, Copenhagen-Munksgaard, 1970, pp. 107-181.
76. F. L. Hirsfeld, Acta Crystallogr., Sect. A 1976, 32, 239.
77. K. N. Trueblood, J. D. Dunitz, Acta Crystallogr., Sect. B 1983, 39, 120.