A macrolactamisation-oxazoline ring forming approach towards the tris- oxazole macrolide core in the ulapualides

Synlett

Volumn , Issue 5, 1999, Pages 533-536

  Kempson, James ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Macrolactamisation; Marine natural products; Oxazolines; Ring formation

Indexed keywords

MACROLIDE; OXAZOLE; OXAZOLINE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ESTERIFICATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032927845     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2671     Document Type: Article

References (28)

1. (a) Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Norma, M.; Noguchi, H.; Sankawa, U. J. Org. Chem., 1989, 54, 1360
2. (b) Kernan, M. R.; Molinski, T. F.; Faulkner, D. J. J. Org. Chem., 1988, 53, 5014.
3. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hashimoto, K. Tetrahedron Lett., 1989, 30, 2809.
4. Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseke, K.; Norma, M. J. Am. Chem. Soc., 1986, 108, 847.
5. Kobayashi, J.; Tsuda, M; Fuse, H.; Sasaki, T.; Mikami, Y. J. Nat. Prod., 1997, 60, 150.
6. Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc., 1986, 108, 846. The stereochemistry depicted for ulapualide A, ie 1, is suggested from molecular modelling studies (see refs 7 and 8)
7. For some discussion of this issue see refs: (a) Ichiba, T.; Yoshida, W. Y.; Scheuer, P. J.; Higa, T.; Gravalos, D. G. J. Am. Chem. Soc., 1991, 113, 3173.
8. (b) Nagatsu, A.; Kajitani, H.; Sakakibara, J. Tetrahedron Lett., 1995, 36, 4097.
9. Moore, R. E.; Patterson, G. M. L.; Mynderse, J. S.; Barchi, J.; Norton, T. R.; Furusawa, E.; Furusawa, S. Pure Appl. Chem., 1986, 58, 263
10. Ishibashi, M.; Moore, R. E.; Patterson, G. M. L.; Xu, C.; Clardy, J. J. Org. Chem., 1986, 51, 5300.
11. Chattopadhyay, S. K.; Pattenden, G. Tetrahedron Lett., 1998, 39, 6095.
12. See Chattopadhyay, S. K.; Pattenden, G. Synlett, 1997, 1345 and extensive references and bibliography contained therein.
13. For the genesis of this approach see: Chattopadhyay, S. K.; Pattenden, G. Synlett, 1997, 1342. For other approaches to the tris-oxazole unit in the ulapualides see: (a) Panek, J. S.; Beresis, R. T.; Celatka, C. A. J. Org. Chem., 1996, 61, 6494.
14. For the genesis of this approach see: Chattopadhyay, S. K.; Pattenden, G. Synlett, 1997, 1342. For other approaches to the tris-oxazole unit in the ulapualides see: (a) Panek, J. S.; Beresis, R. T.; Celatka, C. A. J. Org. Chem., 1996, 61, 6494.
15. (b) Panek, J. S.; Beresis, R. T. J. Org. Chem., 1996, 61, 6496.
16. (c) Liu, P.; Celatka, C. A.; Panek, J. S. Tetrahedron Lett., 1997, 38, 5445.
17. (d) Celatka, C. A.; Liu, P.; Panek, J. S. Tetrahedron Lett., 1997, 38, 5449.
18. (e) Yoo, S-K. Tetrahedron Lett., 1992, 33, 2159. cf Doyle, K. J.; Moody, C. J. Tetrahedron, 1994, 50, 3761.
19. (e) Yoo, S-K. Tetrahedron Lett., 1992, 33, 2159. cf Doyle, K. J.; Moody, C. J. Tetrahedron, 1994, 50, 3761.
20. Comforth, J. W.; Comforth, R. H. J. Chem. Soc., 1947, 96.
21. Danishefsky, S. J.; Pearson, W. H. J. Org. Chem., 1983, 48, 3865.
22. 3 requires M, 468.2134).
23. (a) Garner, P.; Park, J. M. J. Org. Chem., 1987, 52, 2361.
24. (b) McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis, 1994, 31.
25. Atkins, G. M. Jr.; Burgess, E. M. J. Am. Chem. Soc., 1968, 90, 4744.
26. Williams, D. R.; Lowder, P. D.; Gu, Y-G.; Brooks, D. A. Tetrahedron Lett., 1997, 38, 331.
27. Reader, M. PhD Thesis, University of Nottingham, 1996.
28. Evans, D. L.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L. Jr.; Meyers, A. I. J. Org. Chem., 1979, 44, 497.