Chemistry of the mycalamides: Antiviral and antitumour compounds from a New Zealand marine sponge. Part 6. The synthesis and testing of analogues of the C(7)-C(10) fragment

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1997, Pages 1647-1654

  Abell, Andrew D ^a   Blunt, John W ^a   Foulds, Glenn J ^a   Munro, Murray H G ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748667748     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a608168a     Document Type: Article

References (32)

1. Part 1: N. B. Perry, J. W. Blunt, M. H. G. Munro and L. K. Pannell, J. Am. Chem. Soc., 1988, 110, 4850.
2. Part 2: N. B. Perry, J. W. Blunt, M. H. G. Munro and A. M. Thompson, J. Org. Chem., 1990, 55, 223.
3. Part 3: A. M. Thompson, J. W. Blunt, M. H. G. Munro, N. B. Perry and L. K. Pannell, J. Chem. Soc., Perkin Trans. 1, 1992, 1335;
4. Part 4: A. M. Thompson, J. W. Blunt, M. H. G. Munro and B. M. Clark, J. Chem. Soc., Perkin Trans. 1, 1994, 1025;
5. Part 5: A. M. Thompson, J. W. Blunt, M. H. G. Munro and N. B. Perry, J. Chem. Soc., Perkin Trans. 1, 1995, 1233.
6. C. Cardani, D. Ghiringhelli, R. Mondelli and A. Quilico, Tetrahedron Lett., 1965, 2537;
7. C. Cardani, D. Ghiringhelli, A. Quilico and A. Selva, Tetrahedron Lett., 1967, 4023.
8. (a) S. Sakemi, T. Ichiba, S. Kahmoto, G. Saucy and T. Higa, J. Am. Chem. Soc., 1988, 110, 4851;
9. (b) S. Matsunaga, N. Fusetani and Y. Nakao, Tetrahedron, 1992, 48, 8369.
10. N. Fusetani, T. Sugawara and S. Matsunaga, J. Org. Chem., 1992, 57, 3828.
11. T. Nakata, S. Nagao and T. Oishi, Tetrahedron Lett., 1985, 26, 6465.
12. P. Kocienski, K. Jarowicki and S. Marczak, Synthesis, 1991, 1191.
13. C. Y. Hong and Y. Kishi, J. Org. Chem., 1990, 55, 4242;
14. J. Am. Chem. Soc., 1991, 113, 9693.
15. N. S. Burres and J. J. Clement, Cancer Res., 1989, 49, 2935.
16. P. Kocienski, P. Ranbo, J. K. Davis, F. T. Boyle, D. E. Davies and A. Richter, J. Chem. Soc., Perkin Trans. 1, 1996, 1797.
17. F. Matsuda, N. Tomiyoshi, M. Yanagiya and T. Matsumoto, Tetrahedron. 1988, 44, 7063;
18. F. Matsuda, M. Yanagiya and T. Matsumoto, Tetrahedron Lett., 1982, 23, 4043.
19. M. M. Endicott, E. Wick, M. L. Mercury and M. L. Sherrill, J. Am. Chem. Soc., 1946, 68, 1299.
20. L. F. Audrieth and M. Sveda, Org. Synth., 1955, Coll. Vol. 3, 536.
21. F. Klages and E. Mühlbauer, Chem. Ber., 1959, 92, 1818.
22. K. Pilgram and G. E. Pollard, J. Heterocycl. Chem., 1977, 14, 1029.
23. C. E. Redmann and C. Niemann, Org. Synth., 1955, Coll. Vol. 3, 11.
24. T. Ogawa, S. Nakabayashi and S. Shibata, Agric. Biol. Chem., 1983, 47, 281.
25. A. Bertho and J. Maier, Justus Liebigs Ann. Chem., 1932, 498, 50.
26. M. C. Alley, D. A. Scudiero, A. Monks, M. L. Hursey, M. J. Czerwinski, D. L. Fine, B. J. Abbott, J. G. Mayo, R. H. Shoemaker and M. R. Boyd, Cancer Res., 1988, 48, 589.
27. T. Kolasa and M. J. Miller, J. Org. Chem., 1987, 52, 4978.
28. S. Y. Hwang, W. D. Kingsbury, N. M. Hall, D. R. Jakas, G. L. Dunn and C. Gilvarg, Anal. Biochem., 1986, 154, 552.
29. U. Schmidt, P. Gleich, H. Griesser and R. Utz, Synthesis, 1986, 992.
30. G. M. Sheldrick, Program for Crystal Structure Solution, University of Göttingen, 1993.
31. G. M. Sheldrick, Acta Crystallgr., Sect. A, 1990, 46, 467.
32. International Tables for Crystallography, ed. J. A. Ibers and W. C. Hamilton, vol. C, Kynoch Press, Birmingham, 1992.