Synthesis of enamides related to the salicylate antitumor macrolides using copper-mediated vinylic substitution

Organic Letters

Volumn 2, Issue 9, 2000, Pages 1333-1336

  Shen, Ruichao ^a   Porco Jr , John A ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001572533     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005800t     Document Type: Article

References (36)

1. (a) Galinis, D. L.; McKee, T. C.; Pannell, L. K.; Cardellina, J. H., II; Boyd, M. R. J. Org. Chem. 1997, 62, 8968.
2. (b) McKee, T. C.; Galinis, D. L.; Pannell, L. K.; Cardellina, J. H., II; Laasko, J.; Ireland, C. M.; Murray, L.; Capon, R. J.; Boyd, M. R. J. Org. Chem. 1998, 63, 7805.
3. (c) Suzumura et al. have independently isolated YM-75518 which is identical to lobatamide A, see: Suzumura, K.-i.; Takahashi, I.; Matsumoto, H.; Nagai, K.; Setiawan, B.; Rantiamodjo, R. M.; Suzuki, K.-i.; Nagano, N. Tetrahedron Lett. 1997, 38, 7573.
4. Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y. Seto, H. J. Org. Chem. 1999, 64, 153.
5. Erickson, K. L.; Beutler, J.; Cardellina, J. H., II; Boyd, M. R. J. Org. Chem. 1997, 62, 8188.
6. Dekker, K. A.; Aiello, R. J.; Hirai, H.; Inagaki, T.; Sakakibara, T.; Suzuki, Y.; Thompson, J. F.; Yamauchi, Y.; Kojima, N. J. Antibiot. 1998, 51, 14.
7. Kunze, B.; Jansen, R.; Sasse, F.; Hofle, G.; Reichenbach, H. J. Antibiot. 1998, 51, 1075.
8. For the synthesis of an enamide-truncated analogue of salicylihalamide A, see: Furstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215.
9. For a recent synthesis of the heptadienamide side chain of salicylihalamide A and apicularens A and B, see: Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407.
10. Brettle, R.; Mosedale, A. J. J. Chem. Soc., Perkin Trans. I. 1988, 2185.
11. Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S.-I. Tetrahedron Lett. 1992, 33, 6643.
12. (a) Mohre, H.; Kilian, R. Tetrahedron 1969, 25, 5745.
13. (b) Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413.
14. (a) Boeckmann, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250.
15. (a) Zeeza, C. A.; Smith, M. B. Synth. Comm. 1987, 17, 729-40.
16. (b) Kiefel, M. J.; Maddock, J.; Pattenden, G. Tetrahedron Lett. 1992, 33, 3227.
17. (a) Cuevas, J.-C.; Patil, P.; Snieckus, V. Tetrahedron Lett. 1989, 30, 5841.
18. (b) Palomo, C.; Aizpurua, J. M.; Legido, M.; Picard, J. P.; Dunogues, J.; Constantieux, T. Tetrahedron Lett. 1992, 33, 3903.
19. (a) Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron Lett. 1993, 34, 1479.
20. (b) Paterson, I.; Cowden, C.; Watson, C. Synlett 1995, 209.
21. Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443.
22. (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
23. (b) Kiyomori, A.; Marcoux, J.-F.; Doye, S.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
24. (c) Kalanin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986.
25. Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716.
26. (a) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
27. (b) Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
28. http://www.argotech.com/quest (March 27, 2000).
29. -1.
30. Pellegata, R.; Italia, A.; Villa, M. Synthesis 1985, 517.
31. Liu, P.; Panek, J. S. J. Am. Chem. Soc. 2000, 122, 1235.
32. For the synthesis of the oxime of malealdehydic acid, see: Schroeter, S. H.; Appel, R.; Brammer, R.; Schenck, G. O. Justus Liebigs Ann. Chem. 1966, 697, 42.
33. Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 47, 481.
34. Further studies are in progress to determine the mode of decomposition of enamide 9 under basic conditions.
35. (a) Aalten, H. L.; van Koten, G.; Grove, D. M.; Kuilman, T.; Piekstra, O. G.; Hulshof, L. A.; Sheldon, R. A. Tetrahedron 1989, 45, 5565.
36. (b) Matyjaszewski, K.; Wei, M.; Xia, J.; Gaynor, S. G. Macromol. Chem. Phys. 1998, 199, 2289.