Efficient synthesis of the pharmacophore of the highly potent antitumor antibiotic CC-1065

Chemistry - A European Journal

Volumn 4, Issue 8, 1998, Pages 1554-1560

  Tietze, Lutz F ^a   Buhr, Wilm ^a   Looft, Jan ^a   Grote, Thomas ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Antibiotics; Antitumor agents; Cyclizations; Heck reaction; Zirconium

Indexed keywords

EID: 0031826357     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980807)4:8<1554::AID-CHEM1554>3.0.CO;2-J     Document Type: Article

References (42)

1. L. J. Hanka, A. Dietz, S. A. Gerpheide, S. L. Kuentzel, D. G. Martin, J. Antibiot. 1978, 31, 1211.
2. D. L. Boger, D. S. Johnson, Angew. Chem. 1996, 108, 1542, Angew. Chem. Int. Ed. Engl. 1996, 36, 1438.
3. D. L. Boger, D. S. Johnson, Angew. Chem. 1996, 108, 1542, Angew. Chem. Int. Ed. Engl. 1996, 36, 1438.
4. a) S. Borman, Chem. Eng. News 1997, 75, No. 46, 37;
5. b) D. L. Boger, H. Zarrinmayeh, T. Ishizaki, P. A. Kitos, O. Suntornwat, J. Am. Chem. Soc. 1990, 112, 8961;
6. c) L. H. Hurley, M. A. Warpehoski, C. S. Lee, J. P. McGroven, M. A. Mitchell, R. C. Kelly, P. A. Aristoff, Biochemistry 1988, 27, 3886.
7. L. F. Tietze, R. Hannemann, W. Buhr, M. Lögers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Döring, I. Schubert, Angew. Chem. 1996, 108, 2840, Angew. Chem. Int. Ed. Engl. 1996, 35, 2674.
8. L. F. Tietze, R. Hannemann, W. Buhr, M. Lögers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Döring, I. Schubert, Angew. Chem. 1996, 108, 2840, Angew. Chem. Int. Ed. Engl. 1996, 35, 2674.
9. L. N. Jungheim, T. A. Shepherd, Chem. Rev. 1994, 94, 1553.
10. V. L. Reynolds, I. Molineux, D. J. Kaplan, D. H. Swenson, L. H. Hurley, Biochemistry 1985, 24, 6228.
11. a) For a review, see: D. L. Boger, C. W. Boyce, R. Garbaccio, J. A. Goldberg, Chem. Rev. 1997, 97, 787;
12. b) L. F. Tietze, T. Grote, J. Org. Chem. 1994, 59, 192;
13. c) M. Toyota, K. Fukumoto, J. Chem. Soc. Perkin Trans. 1 1992, 547;
14. d) R. J. Sundberg, W. J. Pitts, J. Org. Chem. 1991, 56, 3048;
15. e) D. L. Boger, H. Zarrinmayeh, J. Org. Chem. 1990, 55, 1379;
16. f) P. Martin, Helv. Chim. Acta 1989, 72, 1554;
17. g) P. Magnus, T. Gallagher, J. Schultz, Y.-S. Or, T. P. Ananthanarayan, J. Am. Chem. Soc. 1987, 109, 2706;
18. h) C. J. Moody, M. Pass, C. W. Rees, G. Tojo, J. Chem. Soc. Chem. Commun. 1986, 14, 1062;
19. i) G. A. Kraus, S. Yue, J. Sy, J. Org. Chem. 1985, 50, 283;
20. j) W. Wierenga, J. Am. Chem. Soc. 1981, 103, 5621.
21. A short communication has already appeared: L. F. Tietze, W. Buhr, Angew. Chem. 1995, 107, 1485, Angew. Chem. Int. Ed. Engl. 1995, 34, 1366.
22. A short communication has already appeared: L. F. Tietze, W. Buhr, Angew. Chem. 1995, 107, 1485, Angew. Chem. Int. Ed. Engl. 1995, 34, 1366.
23. a) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371;
24. b) E. Negishi, C. Coperet, S. Ma, S.-J. Liou, F. Liu, Chem. Rev. 1996, 96, 365;
25. c) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473, Angew. Chem. Int. Ed. Engl. 1994, 33, 2379;
26. c) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473, Angew. Chem. Int. Ed. Engl. 1994, 33, 2379;
27. d) T. Sakamoto, Y. Kondo, M. Uchiyama, H. Yamanaka, J. Chem. Soc. Perkin Trans, 1, 1993, 1941.
28. S. L. Buchwald, R. B. Nielsen, Chem. Rev. 1988, 88, 1044.
29. R. Adams, J. Am. Chem. Soc. 1953, 75, 3235.
30. a) J. H. Tidwell, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 11797;
31. b) G. Erker, K. Kropp, J. Am. Chem. Soc 1979, 101, 3659.
32. 2: a) P. C. Wailes, H. Weigold, A. P. Bell, J. Organomet. Chem. 1971, 33, 181; b) P. C. Wailes, H. Weigold, J. Organomet. Chem. 1970, 24, 405.
33. 2: a) P. C. Wailes, H. Weigold, A. P. Bell, J. Organomet. Chem. 1971, 33, 181; b) P. C. Wailes, H. Weigold, J. Organomet. Chem. 1970, 24, 405.
34. T. Takahashi, K. Aoyagi, D. Y. Kondakov, J. Chem. Soc. Chem. Commun. 1994, 747.
35. PM3(tm) in SPARTAN: SPARTAN version 4.0, © Wavefunction, 18401 Von Karman Ave., #370, Irvine, CA 92715 (USA), 1995.
36. a) L. F. Tietze, T. Nöbel, M. Spescha, Angew. Chem. 1996, 108, 2385, Angew. Chem. Int. Ed. Engl. 1996, 35, 2259;
37. a) L. F. Tietze, T. Nöbel, M. Spescha, Angew. Chem. 1996, 108, 2385, Angew. Chem. Int. Ed. Engl. 1996, 35, 2259;
38. b) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2;
39. c) L. F. Tietze, R. Schimpf, Angew. Chem. 1994, 106, 1138, Angew. Chem. Int. Ed. Engl. 1994, 33, 1089;
40. c) L. F. Tietze, R. Schimpf, Angew. Chem. 1994, 106, 1138, Angew. Chem. Int. Ed. Engl. 1994, 33, 1089;
41. d) M. M. Abelman, T. Oh, L. E. Overman, J. Org. Chem. 1987, 52, 4130.
42. O. Mitsunobu, Synthesis, 1981, 1.