Reductive thioalkylation of a pyranonaphthoquinone

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 3, 2000, Pages 317-322

  Brimble, Margaret A ^a,b   Nairn, Michael R ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ANTIBIOTICS; OXIDATION; PH EFFECTS; REDUCTION; TUMORS;

REDUCTIVE THIOALKYLATION;

KETONES;

EID: 0034615203     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908680c     Document Type: Article

References (32)

1. H. Hoeksama and W. C. Kruger, J. Antibiot., 1976, 29, 704.
2. H. Tanaka, Y. Koyama, J. Awaya, H. Marumo, R. Oiwa, M. Katagiri, T. Nagai and S. Omura, J. Antibiot., 1975, 27, 860.
3. S. Omura, H. Tanaka, Y. Okada and H. Marumo, J. Chem. Soc., Chem. Commun., 1976, 320.
4. Y. Iwai, A. Kora, Y. Takahashi, T. Awaya, R. Masuma, R. Oiwa and S. Omura, J. Antibiot., 1978, 31, 959.
5. For a review see: M. A. Brimble, L. J. Duncalf and M. R. Nairn, Nat. Prod. Rep., 1999, 16, 267.
6. H. W. Moore, Science, 1977, 197, 527.
7. H. W. Moore and R. Czerniak, Med. Res. Rev., 1981, 1, 249.
8. For a preliminary communication see: M. A. Brimble and M. R. Nairn, Tetrahedron Lett., 1998, 39, 4879.
9. P. Schiltz and H. Kohn, J. Am. Chem. Soc., 1993, 115, 10510.
10. K. Ramakrishanan and J. Fisher, J. Med. Chem., 1986, 29, 1215.
11. (a) D. J. Taatjes, D. J. Fenick, G. Gaudiano and T. H. Koch, Curr. Pharm. Des., 1998, 4, 203;
12. (b) D. J. Taatjes, G. Gaudiano, K. Resing and T. H. Koch, J. Med. Chem, 1997, 40, 1276.
13. S. R. Angle, J. D. Rainier and C. Woytowicz, J. Org. Chem., 1997, 62, 5884 and references cited therein.
14. M. Tomasz, R. Lipman, D. Chowdary, J. Pawlak, G. L. Verdine and K. Nakanishi, Science, 1987, 235, 1204.
15. D. M. Peterson and J. Fisher, Biochemistry, 1986, 25, 4077.
16. S. Danishefsky and M. Ciufolini, J. Am. Chem. Soc., 1984, 106, 6424.
17. U. Horemann, K. Iguchi, P. J. Keller, J. F. Kozlowski and H. Kohn, J. Org. Chem., 1983, 48, 5026.
18. H. Kohn, N. Zein, X. Q. Lin, J.-Q. Ding and K. M. Kadish, J. Am. Chem. Soc, 1987, 109, 1833.
19. B. M. Hoey, J. Butler and A. J. Swallow, Biochemistry, 1988, 27, 2608.
20. M. A. Brimble and S. J. Stuart, J. Chem. Soc., Perkin Trans, 1, 1990, 881.
21. M. A. Brimble and S. M. Lynds, J. Chem. Soc., Perkin Trans, 1, 1994, 493.
22. M. A. Brimble, L. J. Duncalf and D. Neville, J. Chem. Soc., Perkin Trans. 1, 1998, 4165.
23. M. A. Brimble, M. R. Nairn and J. Park, Org. Lett., in press.
24. R. F. Anderson, M. A. Brimble, M. R. Nairn and J. E. Packer, J. Chem. Soc., Perkin Trans. 2, 1999, 475.
25. (a) I. Han, D. J. Russell and H. Kohn, J. Org. Chem., 1992, 57, 1799;
26. (b) D. J. Russell and H. Kohn, Heterocydes, 1990, 31, 223.
27. V.-S. Li and H. Kohn, J. Am. Chem. Soc., 1991, 113, 275.
28. S. Subramaniam and H. Kohn, J. Am. Chem. Soc., 1993, 115, 10519.
29. (a) Y. P. Hong and H. Kohn, J. Am. Chem. Soc., 1991, 113, 4634;
30. (b) Y. P. Hong and H. Kohn, J. Org. Chem., 1991, 56, 6479.
31. K. Tamaki, S. Kurihara and Y. Sugimura, Tetrahedron Lett., 1993, 34, 8477.
32. F. D. Tropper, F. O. Andersson, S. Cao and R. Roy, J. Carbohydr. Chem., 1992, 11, 741.