Towards a total synthesis of ulapualide A. A concise synthesis of the tris-Oxazole macrolide core and entire carbon skeleton

Synlett

Volumn , Issue 12, 1997, Pages 1345-1348

  Chattopadhyay, Shital K ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002532127     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1055     Document Type: Article

References (28)

1. a) Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, 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. Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M. J. Am. Chem. Soc., 1986, 108, 847.
4. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hashimoto, K. Tetrahedron Lett., 1989, 30, 2809.
5. Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc., 1986, 108, 846.
6. Maddock, J.; Pattenden, G.; Wight, P. G. J. Computer-Aided Molecular Design, 1993, 7, 573.
7. Ishibashi, M.; Moore, R. E.; Patterson, G. M. L.; Xu, C.; Clardy, J. J. Org. Chem., 1986, 51, 5300.
8. Yamada, K.; Ojika, M.; Ishigaki, T.; Yoshida, Y.; Ekimoto, H.; Arakawa, M. J. Am. Chem. Soc., 1993, 115, 11020.
9. Paterson, I.; Watson, C.; Yeung, K-S.; Wallace, P. A.; Ward, R. A. J. Org. Chem., 1997, 62, 452.
10. Kigoshi, H.; Ojika, M.; Ishigaki, T.; Suenaga, K.; Mutuo, T.; 116, 7443.
11. a) Panek, J. S.; Beresis, R. T.; Celatka, C. A. J. Org. Chem., 1996, 61, 6496.
12. c) Celatka, C. A.; Liu, P.; Panek, J. S. Tetrahedron Lett., 1997, 38, 5449.
13. d) Liu, P.; Celatka, C. A.; Panek, J. S. Tetrahedron Lett., 1997, 38, 5445.
14. This synthesis was first presented at the 8th International Symposium on "Marine Natural Products", Tenerife, Canary Islands, Spain, 1995.
15. The carbon skeleton of ulapualide A is numbered as shown in reference 4, reporting its isolation.
16. Presented at the 13th International Congress of Heterocylic Chemistry, Corvallis, Oregon, USA, 1991.
17. Pattenden, G. J. Heterocyclic Chem., 1992, 29, 607.
18. Reader, M. PhD Thesis, University of Nottingham, 1996.
19. Knight, D. W.; Pattenden, G.; Rippon, D. E. Synlett, 1990, 1, 36.
20. Chattopadhyay, S. K.; Pattenden, G. Tetrahedron Lett., 1995, 36, 5271.
21. Guindon, Y.; Yoakim, C.; Morton, H. E. J. Org. Chem., 1984, 49, 3912.
22. All new compounds gave satisfactory spectroscopic data in agreement with the assigned structures and stereochemistries.
23. 2O,r.t.,12h,76%
24. a) Nicolaou, K. C.; Sietz, S. P.; Pavia, M. R. J. Am. Chem. Soc., 1982, 104, 2030.
25. b) Aristoff, P. A. J. Org. Chem., 1981, 46, 1954.
26. Ho, T-L. Synth. Comm., 1978, 8, 15.
27. Friedrich-Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem., 1989, 54, 751.
28. Inanga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn., 1979, 52, 1989.