Solid-phase synthesis of cyclic sulfonamides employing a ring-closing metathesis-cleavage strategy

Tetrahedron Letters

Volumn 41, Issue 19, 2000, Pages 3681-3685

  Brown, Richard C D ^a   Castro, José L ^b   Moriggi, Jean Dominique ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

Linkers; Ring closing metathesis; Solid phase synthesis; Sulfonamides

Indexed keywords

SULFONAMIDE;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; SOLID PHASE EXTRACTION; SYNTHESIS;

EID: 0034611941     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00442-1     Document Type: Article

References (25)

1. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
2. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
3. Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293.
4. James, I. W. Tetrahedron 1999, 55, 4855.
5. Van Maarseveen, J. H. Combinatorial Chemistry and High Throughput Screening 1998, 1, 185.
6. Lam, P. Y.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N.; De Lucca, G. V.; Rodgers, J. D. US Patent 5,610,294, 1997.
7. Handlon, A. L.; Hodgson, G. L.; Hyman, C. E.; Clifton, E. WO Patent 9838182, 1998.
8. Makino, K.; Sato, T.; Morimoto, K.; Akiyama, S.; Suzuki, H.; Suzuki, K.; Nawamaki, T.; Watanabe, S. EP Patent 342456, 1989.
9. The synthesis of some closely related cyclic sulfonamides have recently been reported: Hanson, P. R.; Probst, D. A.; Robinson, R. E.; Yau, M. Tetrahedron Lett. 1999, 40, 4761.
10. Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron 1999, 55, 8189.
11. Veerman, J. J. N.; Van Maarseveen, J. H.; Visser, G. M.; Kruse, C. G.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 1998, 2583.
12. Nicolaou, K. C.; Hepworth, D.; King, N. P.; Finlay, M. R. V. Pure Appl. Chem. 1999, 71, 989.
13. Pernerstorfer, J.; Schuster, M.; Blechert, S. Chem. Commun. 1997, 1949.
14. For related linkers used for the metathesis cleavage of acyclic olefins, see: Peters, J. U.; Blechert, S. Synlett 1997, 348; Knerr, L.; Schmidt, R. R. Synlett 1999, 1802.
15. For related linkers used for the metathesis cleavage of acyclic olefins, see: Peters, J. U.; Blechert, S. Synlett 1997, 348; Knerr, L.; Schmidt, R. R. Synlett 1999, 1802.
16. Deslongchamps, P.; Lamothe, S.; Lin, H. Can. J. Chem. 1987, 65, 1298.
17. King, J. F.; Harding, R. D. K. J. Am. Chem. Soc. 1976, 98, 3312.
18. King, J. F.; Harding, R. D. K. J. Am. Chem. Soc. 1976, 98, 3312.
19. Neustadt, B. R. Tetrahedron Lett. 1994, 35, 379.
20. Brown, R. C. D.; Fisher, M. Chem. Commun. 1999, 1547.
21. Castro, J. L.; Matassa, V. G.; Ball, R. G. J. Org. Chem. 1994, 59, 2289.
22. Frechet, J. M.; Schuerch, C. J. Am. Chem. Soc. 1971, 93, 492.
23. Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657.
24. Beaver, K. A.; Siegmund, A. C.; Spear, K. L. Tetrahedron Lett. 1996, 37, 1145.
25. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746.