Ring-closing metathesis: Development of a cyclisation-cleavage strategy for the solid-phase synthesis of cyclic sulfonamides

Organic and Biomolecular Chemistry

Volumn 2, Issue 6, 2004, Pages 835-844

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

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^c Inpharzam Ricerche SA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; COMPLEXATION; FILTRATION; INFRARED SPECTROSCOPY; POLYSTYRENES; REDUCTION;

COMBINATORIAL CHEMISTRY; RING-CLOSING METATHESIS; SOLID-PHASE CYCLIZATION-CLEAVAGE;

SULFUR COMPOUNDS;

EID: 1842586978     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b313686h     Document Type: Article

References (79)

1. (a) P. Seneci and S. Miertus, Mol. Divers., 2000, 5, 75;
2. (b) R. E. Dolle, J. Comb. Chem., 2000, 2, 383;
3. (c) N. K. Terrett, M. Gardner, D. W. Gordon, R. J. Kobylecki and J. Steele, Tetrahedron, 1995, 51, 8135;
4. (d) L. A. Thompson and J. A. Ellman, Chem. Rev., 1996, 96, 555;
5. (e) S. Booth, P. H. H. Hermkens, H. C. J. Ottenheijm and D. C. Rees, Tetrahedron, 1998, 54, 15385;
6. (f) A. R. Brown, P. H. H. Hermkens, H. C. J. Ottenheijm and D. C. Rees, Synlett, 1998, 817;
7. (g) R. C. D. Brown, J. Chem. Soc., Perkin Trans. 1, 1998, 3293;
8. (h) J. W. Corbett, Org. Prep. Proced. Int., 1998, 30, 489;
9. (i) J. S. Fruchtel and G. Jung, Angew. Chem., Int. Ed. Engl., 1996, 35, 17;
10. (j) P. H. H. Hermkens, H. C. J. Ottenheijm and D. Rees, Tetrahedron, 1996, 52, 4527;
11. (k) P. H. H. Hermkens, H. C. J. Ottenheijm and D. C. Rees, Tetrahedron, 1997, 53, 5643;
12. (l) B. A. Lorsbach and M. J. Kurth, Chem. Rev., 1999, 99, 1549;
13. (m) A. Nefzi, J. M. Ostresh and R. A. Houghten, Chem. Rev., 1997, 97, 449.
14. (a) S. Brase and S. Dahmen, Chem. Eur. J., 2000, 6, 1899;
15. (b) F. Guillier, D. Drain and M. Bradley, Chem. Rev., 2000, 100, 2091;
16. (c) I. W. James, Tetrahedron, 1999, 55, 4855;
17. F. Zaragoza, Angew. Chem., Int. Ed., 2000, 39, 2077;
18. (e) P. Blaney, R. Grig and V. Sridharan, Chem. Rev., 2002, 102, 2607.
19. See references 2a-e and: (a) J. H. van Maarseveen, Comb. Chem. High Throughput Screen, 1998, 1, 185;
20. (b) K. H. Park and M. J. Kurth, Drug Future, 2000, 25, 1265.
21. For a selection of olefln metathesis reviews: (a) R. H. Grubbs, S. J. Miller and G. C. Fu, Ace. Chem. Res., 1995, 28, 446; (b) M. Schuster and S. Blechert, Angew. Chem. Int. Ed. Engl, 1997, 36, 2037; (c) S. A. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (d) A. J. Phillips and A. D. Abell, Aldrichimica Acta, 1999, 32, 75; (e) A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012; (f) S. J. Connon and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900.
22. For a selection of olefln metathesis reviews: (a) R. H. Grubbs, S. J. Miller and G. C. Fu, Ace. Chem. Res., 1995, 28, 446; (b) M. Schuster and S. Blechert, Angew. Chem. Int. Ed. Engl, 1997, 36, 2037; (c) S. A. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (d) A. J. Phillips and A. D. Abell, Aldrichimica Acta, 1999, 32, 75; (e) A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012; (f) S. J. Connon and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900.
23. For a selection of olefln metathesis reviews: (a) R. H. Grubbs, S. J. Miller and G. C. Fu, Ace. Chem. Res., 1995, 28, 446; (b) M. Schuster and S. Blechert, Angew. Chem. Int. Ed. Engl, 1997, 36, 2037; (c) S. A. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (d) A. J. Phillips and A. D. Abell, Aldrichimica Acta, 1999, 32, 75; (e) A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012; (f) S. J. Connon and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900.
24. For a selection of olefln metathesis reviews: (a) R. H. Grubbs, S. J. Miller and G. C. Fu, Ace. Chem. Res., 1995, 28, 446; (b) M. Schuster and S. Blechert, Angew. Chem. Int. Ed. Engl, 1997, 36, 2037; (c) S. A. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (d) A. J. Phillips and A. D. Abell, Aldrichimica Acta, 1999, 32, 75; (e) A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012; (f) S. J. Connon and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900.
25. For a selection of olefln metathesis reviews: (a) R. H. Grubbs, S. J. Miller and G. C. Fu, Ace. Chem. Res., 1995, 28, 446; (b) M. Schuster and S. Blechert, Angew. Chem. Int. Ed. Engl, 1997, 36, 2037; (c) S. A. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (d) A. J. Phillips and A. D. Abell, Aldrichimica Acta, 1999, 32, 75; (e) A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012; (f) S. J. Connon and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900.
26. For a selection of olefln metathesis reviews: (a) R. H. Grubbs, S. J. Miller and G. C. Fu, Ace. Chem. Res., 1995, 28, 446; (b) M. Schuster and S. Blechert, Angew. Chem. Int. Ed. Engl, 1997, 36, 2037; (c) S. A. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (d) A. J. Phillips and A. D. Abell, Aldrichimica Acta, 1999, 32, 75; (e) A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012; (f) S. J. Connon and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900.
27. For previous examples of cyclisation cleavage using RCM: (a) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser and C. G. Kruse, Tetrahedron Lett., 1996, 37, 8249; (b) J. Pernerstorfer, M. Schuster and S. Blechert, Chem. Commun, 1997, 1949; (c) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron Lett., 1997, 38, 7143; (d) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268; (e) A. D. Piscopio, J. F. Miller and K., Koch, Tetrahedron Lett., 1998, 39, 2667; (f) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Eur. J. Org. Chem., 1998, 2583; (g) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron, 1999, 55, 8189; (h) R. C. D. Brown, J. L. Castro and J. D. Moriggi, Tetrahedron Lett., 2000, 41, 3681; (i) S. Sasmal, A. Geyer and M. E. Maier, J. Org. Chem., 2002, 67,; 6260.
28. For previous examples of cyclisation cleavage using RCM: (a) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser and C. G. Kruse, Tetrahedron Lett., 1996, 37, 8249; (b) J. Pernerstorfer, M. Schuster and S. Blechert, Chem. Commun, 1997, 1949; (c) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron Lett., 1997, 38, 7143; (d) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268; (e) A. D. Piscopio, J. F. Miller and K., Koch, Tetrahedron Lett., 1998, 39, 2667; (f) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Eur. J. Org. Chem., 1998, 2583; (g) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron, 1999, 55, 8189; (h) R. C. D. Brown, J. L. Castro and J. D. Moriggi, Tetrahedron Lett., 2000, 41, 3681; (i) S. Sasmal, A. Geyer and M. E. Maier, J. Org. Chem., 2002, 67,; 6260.
29. For previous examples of cyclisation cleavage using RCM: (a) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser and C. G. Kruse, Tetrahedron Lett., 1996, 37, 8249; (b) J. Pernerstorfer, M. Schuster and S. Blechert, Chem. Commun, 1997, 1949; (c) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron Lett., 1997, 38, 7143; (d) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268; (e) A. D. Piscopio, J. F. Miller and K., Koch, Tetrahedron Lett., 1998, 39, 2667; (f) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Eur. J. Org. Chem., 1998, 2583; (g) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron, 1999, 55, 8189; (h) R. C. D. Brown, J. L. Castro and J. D. Moriggi, Tetrahedron Lett., 2000, 41, 3681; (i) S. Sasmal, A. Geyer and M. E. Maier, J. Org. Chem., 2002, 67,; 6260.
30. For previous examples of cyclisation cleavage using RCM: (a) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser and C. G. Kruse, Tetrahedron Lett., 1996, 37, 8249; (b) J. Pernerstorfer, M. Schuster and S. Blechert, Chem. Commun, 1997, 1949; (c) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron Lett., 1997, 38, 7143; (d) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268; (e) A. D. Piscopio, J. F. Miller and K., Koch, Tetrahedron Lett., 1998, 39, 2667; (f) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Eur. J. Org. Chem., 1998, 2583; (g) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron, 1999, 55, 8189; (h) R. C. D. Brown, J. L. Castro and J. D. Moriggi, Tetrahedron Lett., 2000, 41, 3681; (i) S. Sasmal, A. Geyer and M. E. Maier, J. Org. Chem., 2002, 67,; 6260.
31. For previous examples of cyclisation cleavage using RCM: (a) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser and C. G. Kruse, Tetrahedron Lett., 1996, 37, 8249; (b) J. Pernerstorfer, M. Schuster and S. Blechert, Chem. Commun, 1997, 1949; (c) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron Lett., 1997, 38, 7143; (d) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268; (e) A. D. Piscopio, J. F. Miller and K., Koch, Tetrahedron Lett., 1998, 39, 2667; (f) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Eur. J. Org. Chem., 1998, 2583; (g) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron, 1999, 55, 8189; (h) R. C. D. Brown, J. L. Castro and J. D. Moriggi, Tetrahedron Lett., 2000, 41, 3681; (i) S. Sasmal, A. Geyer and M. E. Maier, J. Org. Chem., 2002, 67,; 6260.
32. For previous examples of cyclisation cleavage using RCM: (a) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser and C. G. Kruse, Tetrahedron Lett., 1996, 37, 8249; (b) J. Pernerstorfer, M. Schuster and S. Blechert, Chem. Commun, 1997, 1949; (c) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron Lett., 1997, 38, 7143; (d) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268; (e) A. D. Piscopio, J. F. Miller and K., Koch, Tetrahedron Lett., 1998, 39, 2667; (f) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Eur. J. Org. Chem., 1998, 2583; (g) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron, 1999, 55, 8189; (h) R. C. D. Brown, J. L. Castro and J. D. Moriggi, Tetrahedron Lett., 2000, 41, 3681; (i) S. Sasmal, A. Geyer and M. E. Maier, J. Org. Chem., 2002, 67,; 6260.
33. For previous examples of cyclisation cleavage using RCM: (a) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser and C. G. Kruse, Tetrahedron Lett., 1996, 37, 8249; (b) J. Pernerstorfer, M. Schuster and S. Blechert, Chem. Commun, 1997, 1949; (c) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron Lett., 1997, 38, 7143; (d) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268; (e) A. D. Piscopio, J. F. Miller and K., Koch, Tetrahedron Lett., 1998, 39, 2667; (f) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Eur. J. Org. Chem., 1998, 2583; (g) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron, 1999, 55, 8189; (h) R. C. D. Brown, J. L. Castro and J. D. Moriggi, Tetrahedron Lett., 2000, 41, 3681; (i) S. Sasmal, A. Geyer and M. E. Maier, J. Org. Chem., 2002, 67,; 6260.
34. For previous examples of cyclisation cleavage using RCM: (a) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser and C. G. Kruse, Tetrahedron Lett., 1996, 37, 8249; (b) J. Pernerstorfer, M. Schuster and S. Blechert, Chem. Commun, 1997, 1949; (c) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron Lett., 1997, 38, 7143; (d) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268; (e) A. D. Piscopio, J. F. Miller and K., Koch, Tetrahedron Lett., 1998, 39, 2667; (f) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Eur. J. Org. Chem., 1998, 2583; (g) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron, 1999, 55, 8189; (h) R. C. D. Brown, J. L. Castro and J. D. Moriggi, Tetrahedron Lett., 2000, 41, 3681; (i) S. Sasmal, A. Geyer and M. E. Maier, J. Org. Chem., 2002, 67,; 6260.
35. For previous examples of cyclisation cleavage using RCM: (a) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser and C. G. Kruse, Tetrahedron Lett., 1996, 37, 8249; (b) J. Pernerstorfer, M. Schuster and S. Blechert, Chem. Commun, 1997, 1949; (c) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron Lett., 1997, 38, 7143; (d) K. C. Nicolaou, N. Wissinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268; (e) A. D. Piscopio, J. F. Miller and K., Koch, Tetrahedron Lett., 1998, 39, 2667; (f) J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Eur. J. Org. Chem., 1998, 2583; (g) A. D. Piscopio, J. F. Miller and K. Koch, Tetrahedron, 1999, 55, 8189; (h) R. C. D. Brown, J. L. Castro and J. D. Moriggi, Tetrahedron Lett., 2000, 41, 3681; (i) S. Sasmal, A. Geyer and M. E. Maier, J. Org. Chem., 2002, 67,; 6260.
36. For RCM-based cleavage approaches to release acyclic olefins from a diene linker: (a) J.-U. Peters and S. Blechert, Synlett, 1997, 348; (b) L. Knerr and R. R. Schmidt, Synlett, 1999, 1802; (c) L. Knerr and R. R. Schmidt, Eur. J. Org. Chem., 2000, 2803; (d) D. Brohm, S. Metzger, A. Bhargava, O. Müller, F. Lieb and H. Waldmann, Angew. Chem., Int. Ed., 2002, 41, 307.
37. For RCM-based cleavage approaches to release acyclic olefins from a diene linker: (a) J.-U. Peters and S. Blechert, Synlett, 1997, 348; (b) L. Knerr and R. R. Schmidt, Synlett, 1999, 1802; (c) L. Knerr and R. R. Schmidt, Eur. J. Org. Chem., 2000, 2803; (d) D. Brohm, S. Metzger, A. Bhargava, O. Müller, F. Lieb and H. Waldmann, Angew. Chem., Int. Ed., 2002, 41, 307.
38. For RCM-based cleavage approaches to release acyclic olefins from a diene linker: (a) J.-U. Peters and S. Blechert, Synlett, 1997, 348; (b) L. Knerr and R. R. Schmidt, Synlett, 1999, 1802; (c) L. Knerr and R. R. Schmidt, Eur. J. Org. Chem., 2000, 2803; (d) D. Brohm, S. Metzger, A. Bhargava, O. Müller, F. Lieb and H. Waldmann, Angew. Chem., Int. Ed., 2002, 41, 307.
39. For RCM-based cleavage approaches to release acyclic olefins from a diene linker: (a) J.-U. Peters and S. Blechert, Synlett, 1997, 348; (b) L. Knerr and R. R. Schmidt, Synlett, 1999, 1802; (c) L. Knerr and R. R. Schmidt, Eur. J. Org. Chem., 2000, 2803; (d) D. Brohm, S. Metzger, A. Bhargava, O. Müller, F. Lieb and H. Waldmann, Angew. Chem., Int. Ed., 2002, 41, 307.
40. For selected examples of RCM on the solid-phase: (a) S. J. Miller, H. E. Blackwell and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 9606; (b) M. Schuster, J. Pernerstorfer and S. Blechert, Angew. Chem., Int. Ed. Engl., 1996, 35, 1979; (c) J. Pernerstorfer, M. Schuster and S. Blechert, Synthesis, 1999, 138; (d) K. Koide, J. M. Finkelstein, Z. Ball and G. L. Verdine, J. Am. Chem. Soc., 2001, 123, 398.
41. For selected examples of RCM on the solid-phase: (a) S. J. Miller, H. E. Blackwell and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 9606; (b) M. Schuster, J. Pernerstorfer and S. Blechert, Angew. Chem., Int. Ed. Engl., 1996, 35, 1979; (c) J. Pernerstorfer, M. Schuster and S. Blechert, Synthesis, 1999, 138; (d) K. Koide, J. M. Finkelstein, Z. Ball and G. L. Verdine, J. Am. Chem. Soc., 2001, 123, 398.
42. For selected examples of RCM on the solid-phase: (a) S. J. Miller, H. E. Blackwell and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 9606; (b) M. Schuster, J. Pernerstorfer and S. Blechert, Angew. Chem., Int. Ed. Engl., 1996, 35, 1979; (c) J. Pernerstorfer, M. Schuster and S. Blechert, Synthesis, 1999, 138; (d) K. Koide, J. M. Finkelstein, Z. Ball and G. L. Verdine, J. Am. Chem. Soc., 2001, 123, 398.
43. For selected examples of RCM on the solid-phase: (a) S. J. Miller, H. E. Blackwell and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 9606; (b) M. Schuster, J. Pernerstorfer and S. Blechert, Angew. Chem., Int. Ed. Engl., 1996, 35, 1979; (c) J. Pernerstorfer, M. Schuster and S. Blechert, Synthesis, 1999, 138; (d) K. Koide, J. M. Finkelstein, Z. Ball and G. L. Verdine, J. Am. Chem. Soc., 2001, 123, 398.
44. G. A. Patani and E. J. LaVoie, Chem. Rev., 1996, 96, 3147.
45. For some selected examples of sulfonamide replacements: HIV protease inhibitors: (a) M. L. Vazquez, M. L. Bryant, M. Clare, G. A. DeCrescenzo, E. M. Doherty, J. N. Freskos, D. P. Getman, K. A. Houseman, J. A. Julien, G. P. Kocan, R. A. Mueller, H.-S. Shieh, W. C. Stallings, R. A. Stegeman and J. J. Talley, J. Med. Chem., 1995, 38, 581; (b) Peptidomimetics: J. Gante, Angew. Chem., Int. Ed., 1994, 33, 1699; (c) W. J. Moree, G. A. van der Marel and R. J. Liskamp, J Org. Chem., 1995, 60, 5157; (d) M. Gude, U. Piarulli, D. Potenza, B. Salom and C. Gennari, Tetrahedron Lett., 1996, 37, 8589; (e) C. Gennari, C. Longari, S. Ressel, B. Salom, U. Piarulli, S. Ceccarelli and A. Mielgo, Eur. J. Org. Chem., 1998, 2437; (f) D. B. A. de Bont, K. M. Sliedregt-Bol, L. J. F. Hofmeyer; and R. M. J. Liskamp, Bioorg. Med. Chem., 1999, 7, 1043; (g) J. van Ameijde and R. M. J. Liskamp, Tetrahedron Lett, 2000, 41, 1103; (h) Leukocyte adhesion inhibitors: K. G. Carson, C. F. Schwender, H. N. Shroff, N. A. Cochran, D. L. Gallant and M. J. Briskin, Bioorg. Med. Chem. Lett., 1997, 7, 711.
46. For some selected examples of sulfonamide replacements: HIV protease inhibitors: (a) M. L. Vazquez, M. L. Bryant, M. Clare, G. A. DeCrescenzo, E. M. Doherty, J. N. Freskos, D. P. Getman, K. A. Houseman, J. A. Julien, G. P. Kocan, R. A. Mueller, H.-S. Shieh, W. C. Stallings, R. A. Stegeman and J. J. Talley, J. Med. Chem., 1995, 38, 581; (b) Peptidomimetics: J. Gante, Angew. Chem., Int. Ed., 1994, 33, 1699; (c) W. J. Moree, G. A. van der Marel and R. J. Liskamp, J Org. Chem., 1995, 60, 5157; (d) M. Gude, U. Piarulli, D. Potenza, B. Salom and C. Gennari, Tetrahedron Lett., 1996, 37, 8589; (e) C. Gennari, C. Longari, S. Ressel, B. Salom, U. Piarulli, S. Ceccarelli and A. Mielgo, Eur. J. Org. Chem., 1998, 2437; (f) D. B. A. de Bont, K. M. Sliedregt-Bol, L. J. F. Hofmeyer; and R. M. J. Liskamp, Bioorg. Med. Chem., 1999, 7, 1043; (g) J. van Ameijde and R. M. J. Liskamp, Tetrahedron Lett, 2000, 41, 1103; (h) Leukocyte adhesion inhibitors: K. G. Carson, C. F. Schwender, H. N. Shroff, N. A. Cochran, D. L. Gallant and M. J. Briskin, Bioorg. Med. Chem. Lett., 1997, 7, 711.
47. For some selected examples of sulfonamide replacements: HIV protease inhibitors: (a) M. L. Vazquez, M. L. Bryant, M. Clare, G. A. DeCrescenzo, E. M. Doherty, J. N. Freskos, D. P. Getman, K. A. Houseman, J. A. Julien, G. P. Kocan, R. A. Mueller, H.-S. Shieh, W. C. Stallings, R. A. Stegeman and J. J. Talley, J. Med. Chem., 1995, 38, 581; (b) Peptidomimetics: J. Gante, Angew. Chem., Int. Ed., 1994, 33, 1699; (c) W. J. Moree, G. A. van der Marel and R. J. Liskamp, J Org. Chem., 1995, 60, 5157; (d) M. Gude, U. Piarulli, D. Potenza, B. Salom and C. Gennari, Tetrahedron Lett., 1996, 37, 8589; (e) C. Gennari, C. Longari, S. Ressel, B. Salom, U. Piarulli, S. Ceccarelli and A. Mielgo, Eur. J. Org. Chem., 1998, 2437; (f) D. B. A. de Bont, K. M. Sliedregt-Bol, L. J. F. Hofmeyer; and R. M. J. Liskamp, Bioorg. Med. Chem., 1999, 7, 1043; (g) J. van Ameijde and R. M. J. Liskamp, Tetrahedron Lett, 2000, 41, 1103; (h) Leukocyte adhesion inhibitors: K. G. Carson, C. F. Schwender, H. N. Shroff, N. A. Cochran, D. L. Gallant and M. J. Briskin, Bioorg. Med. Chem. Lett., 1997, 7, 711.
48. For some selected examples of sulfonamide replacements: HIV protease inhibitors: (a) M. L. Vazquez, M. L. Bryant, M. Clare, G. A. DeCrescenzo, E. M. Doherty, J. N. Freskos, D. P. Getman, K. A. Houseman, J. A. Julien, G. P. Kocan, R. A. Mueller, H.-S. Shieh, W. C. Stallings, R. A. Stegeman and J. J. Talley, J. Med. Chem., 1995, 38, 581; (b) Peptidomimetics: J. Gante, Angew. Chem., Int. Ed., 1994, 33, 1699; (c) W. J. Moree, G. A. van der Marel and R. J. Liskamp, J Org. Chem., 1995, 60, 5157; (d) M. Gude, U. Piarulli, D. Potenza, B. Salom and C. Gennari, Tetrahedron Lett., 1996, 37, 8589; (e) C. Gennari, C. Longari, S. Ressel, B. Salom, U. Piarulli, S. Ceccarelli and A. Mielgo, Eur. J. Org. Chem., 1998, 2437; (f) D. B. A. de Bont, K. M. Sliedregt-Bol, L. J. F. Hofmeyer; and R. M. J. Liskamp, Bioorg. Med. Chem., 1999, 7, 1043; (g) J. van Ameijde and R. M. J. Liskamp, Tetrahedron Lett, 2000, 41, 1103; (h) Leukocyte adhesion inhibitors: K. G. Carson, C. F. Schwender, H. N. Shroff, N. A. Cochran, D. L. Gallant and M. J. Briskin, Bioorg. Med. Chem. Lett., 1997, 7, 711.
49. For some selected examples of sulfonamide replacements: HIV protease inhibitors: (a) M. L. Vazquez, M. L. Bryant, M. Clare, G. A. DeCrescenzo, E. M. Doherty, J. N. Freskos, D. P. Getman, K. A. Houseman, J. A. Julien, G. P. Kocan, R. A. Mueller, H.-S. Shieh, W. C. Stallings, R. A. Stegeman and J. J. Talley, J. Med. Chem., 1995, 38, 581; (b) Peptidomimetics: J. Gante, Angew. Chem., Int. Ed., 1994, 33, 1699; (c) W. J. Moree, G. A. van der Marel and R. J. Liskamp, J Org. Chem., 1995, 60, 5157; (d) M. Gude, U. Piarulli, D. Potenza, B. Salom and C. Gennari, Tetrahedron Lett., 1996, 37, 8589; (e) C. Gennari, C. Longari, S. Ressel, B. Salom, U. Piarulli, S. Ceccarelli and A. Mielgo, Eur. J. Org. Chem., 1998, 2437; (f) D. B. A. de Bont, K. M. Sliedregt-Bol, L. J. F. Hofmeyer; and R. M. J. Liskamp, Bioorg. Med. Chem., 1999, 7, 1043; (g) J. van Ameijde and R. M. J. Liskamp, Tetrahedron Lett, 2000, 41, 1103; (h) Leukocyte adhesion inhibitors: K. G. Carson, C. F. Schwender, H. N. Shroff, N. A. Cochran, D. L. Gallant and M. J. Briskin, Bioorg. Med. Chem. Lett., 1997, 7, 711.
50. For some selected examples of sulfonamide replacements: HIV protease inhibitors: (a) M. L. Vazquez, M. L. Bryant, M. Clare, G. A. DeCrescenzo, E. M. Doherty, J. N. Freskos, D. P. Getman, K. A. Houseman, J. A. Julien, G. P. Kocan, R. A. Mueller, H.-S. Shieh, W. C. Stallings, R. A. Stegeman and J. J. Talley, J. Med. Chem., 1995, 38, 581; (b) Peptidomimetics: J. Gante, Angew. Chem., Int. Ed., 1994, 33, 1699; (c) W. J. Moree, G. A. van der Marel and R. J. Liskamp, J Org. Chem., 1995, 60, 5157; (d) M. Gude, U. Piarulli, D. Potenza, B. Salom and C. Gennari, Tetrahedron Lett., 1996, 37, 8589; (e) C. Gennari, C. Longari, S. Ressel, B. Salom, U. Piarulli, S. Ceccarelli and A. Mielgo, Eur. J. Org. Chem., 1998, 2437; (f) D. B. A. de Bont, K. M. Sliedregt-Bol, L. J. F. Hofmeyer; and R. M. J. Liskamp, Bioorg. Med. Chem., 1999, 7, 1043; (g) J. van Ameijde and R. M. J. Liskamp, Tetrahedron Lett, 2000, 41, 1103; (h) Leukocyte adhesion inhibitors: K. G. Carson, C. F. Schwender, H. N. Shroff, N. A. Cochran, D. L. Gallant and M. J. Briskin, Bioorg. Med. Chem. Lett., 1997, 7, 711.
51. For some selected examples of sulfonamide replacements: HIV protease inhibitors: (a) M. L. Vazquez, M. L. Bryant, M. Clare, G. A. DeCrescenzo, E. M. Doherty, J. N. Freskos, D. P. Getman, K. A. Houseman, J. A. Julien, G. P. Kocan, R. A. Mueller, H.-S. Shieh, W. C. Stallings, R. A. Stegeman and J. J. Talley, J. Med. Chem., 1995, 38, 581; (b) Peptidomimetics: J. Gante, Angew. Chem., Int. Ed., 1994, 33, 1699; (c) W. J. Moree, G. A. van der Marel and R. J. Liskamp, J Org. Chem., 1995, 60, 5157; (d) M. Gude, U. Piarulli, D. Potenza, B. Salom and C. Gennari, Tetrahedron Lett., 1996, 37, 8589; (e) C. Gennari, C. Longari, S. Ressel, B. Salom, U. Piarulli, S. Ceccarelli and A. Mielgo, Eur. J. Org. Chem., 1998, 2437; (f) D. B. A. de Bont, K. M. Sliedregt-Bol, L. J. F. Hofmeyer; and R. M. J. Liskamp, Bioorg. Med. Chem., 1999, 7, 1043; (g) J. van Ameijde and R. M. J. Liskamp, Tetrahedron Lett, 2000, 41, 1103; (h) Leukocyte adhesion inhibitors: K. G. Carson, C. F. Schwender, H. N. Shroff, N. A. Cochran, D. L. Gallant and M. J. Briskin, Bioorg. Med. Chem. Lett., 1997, 7, 711.
52. For some selected examples of sulfonamide replacements: HIV protease inhibitors: (a) M. L. Vazquez, M. L. Bryant, M. Clare, G. A. DeCrescenzo, E. M. Doherty, J. N. Freskos, D. P. Getman, K. A. Houseman, J. A. Julien, G. P. Kocan, R. A. Mueller, H.-S. Shieh, W. C. Stallings, R. A. Stegeman and J. J. Talley, J. Med. Chem., 1995, 38, 581; (b) Peptidomimetics: J. Gante, Angew. Chem., Int. Ed., 1994, 33, 1699; (c) W. J. Moree, G. A. van der Marel and R. J. Liskamp, J Org. Chem., 1995, 60, 5157; (d) M. Gude, U. Piarulli, D. Potenza, B. Salom and C. Gennari, Tetrahedron Lett., 1996, 37, 8589; (e) C. Gennari, C. Longari, S. Ressel, B. Salom, U. Piarulli, S. Ceccarelli and A. Mielgo, Eur. J. Org. Chem., 1998, 2437; (f) D. B. A. de Bont, K. M. Sliedregt-Bol, L. J. F. Hofmeyer; and R. M. J. Liskamp, Bioorg. Med. Chem., 1999, 7, 1043; (g) J. van Ameijde and R. M. J. Liskamp, Tetrahedron Lett, 2000, 41, 1103; (h) Leukocyte adhesion inhibitors: K. G. Carson, C. F. Schwender, H. N. Shroff, N. A. Cochran, D. L. Gallant and M. J. Briskin, Bioorg. Med. Chem. Lett., 1997, 7, 711.
53. For examples of biologically active cyclic sulfonamides: Cyclooxygenase inhibitors: (a) E. S. Lazer, C. K. Miao, C. L. Cywin, R. Sorcek, H.-C. Wong, Z. Meng, I. Potocki, M. Hoermann, R. J. Snow, M. A. Tschantz, T. A. Kelly, D. W. MCNeill, S. J. Coutts, L. Churchill, A. G. Graham, E. David, P.f M. Grob, W. Engel, H. Meier and G. Trummlitz, J. Med. Chem., 1997, 40, 980; (b) HIV protease inhibitors: P. Y. Lam, P. K. Jadhav, C. J. Eyermann, C. N. Hodge, G. V. De Lucca and J. D. Rodgers, USP, 5610294/ 1997; (c) bile acid uptake inhibitors: A. L. Handlon, G. L. Hodgson, C. E. Hyman and E. Clifton, WO 9838182/1998; (d) herbicides: K. Makino, T. Sato, K. Morimoto, S. Akiyama, H. Suzuki, K. Suzuki, T. Nawamaki and S. Watanabe, EP 342456/1989.
54. For examples of biologically active cyclic sulfonamides: Cyclooxygenase inhibitors: (a) E. S. Lazer, C. K. Miao, C. L. Cywin, R. Sorcek, H.-C. Wong, Z. Meng, I. Potocki, M. Hoermann, R. J. Snow, M. A. Tschantz, T. A. Kelly, D. W. MCNeill, S. J. Coutts, L. Churchill, A. G. Graham, E. David, P.f M. Grob, W. Engel, H. Meier and G. Trummlitz, J. Med. Chem., 1997, 40, 980; (b) HIV protease inhibitors: P. Y. Lam, P. K. Jadhav, C. J. Eyermann, C. N. Hodge, G. V. De Lucca and J. D. Rodgers, USP, 5610294/ 1997; (c) bile acid uptake inhibitors: A. L. Handlon, G. L. Hodgson, C. E. Hyman and E. Clifton, WO 9838182/1998; (d) herbicides: K. Makino, T. Sato, K. Morimoto, S. Akiyama, H. Suzuki, K. Suzuki, T. Nawamaki and S. Watanabe, EP 342456/1989.
55. For examples of biologically active cyclic sulfonamides: Cyclooxygenase inhibitors: (a) E. S. Lazer, C. K. Miao, C. L. Cywin, R. Sorcek, H.-C. Wong, Z. Meng, I. Potocki, M. Hoermann, R. J. Snow, M. A. Tschantz, T. A. Kelly, D. W. MCNeill, S. J. Coutts, L. Churchill, A. G. Graham, E. David, P.f M. Grob, W. Engel, H. Meier and G. Trummlitz, J. Med. Chem., 1997, 40, 980; (b) HIV protease inhibitors: P. Y. Lam, P. K. Jadhav, C. J. Eyermann, C. N. Hodge, G. V. De Lucca and J. D. Rodgers, USP, 5610294/ 1997; (c) bile acid uptake inhibitors: A. L. Handlon, G. L. Hodgson, C. E. Hyman and E. Clifton, WO 9838182/1998; (d) herbicides: K. Makino, T. Sato, K. Morimoto, S. Akiyama, H. Suzuki, K. Suzuki, T. Nawamaki and S. Watanabe, EP 342456/1989.
56. For examples of biologically active cyclic sulfonamides: Cyclooxygenase inhibitors: (a) E. S. Lazer, C. K. Miao, C. L. Cywin, R. Sorcek, H.-C. Wong, Z. Meng, I. Potocki, M. Hoermann, R. J. Snow, M. A. Tschantz, T. A. Kelly, D. W. MCNeill, S. J. Coutts, L. Churchill, A. G. Graham, E. David, P.f M. Grob, W. Engel, H. Meier and G. Trummlitz, J. Med. Chem., 1997, 40, 980; (b) HIV protease inhibitors: P. Y. Lam, P. K. Jadhav, C. J. Eyermann, C. N. Hodge, G. V. De Lucca and J. D. Rodgers, USP, 5610294/ 1997; (c) bile acid uptake inhibitors: A. L. Handlon, G. L. Hodgson, C. E. Hyman and E. Clifton, WO 9838182/1998; (d) herbicides: K. Makino, T. Sato, K. Morimoto, S. Akiyama, H. Suzuki, K. Suzuki, T. Nawamaki and S. Watanabe, EP 342456/1989.
57. For the first synthesis of 6- and 7-membered sultams in solution using a RCM approach see: (a) P. R. Hanson, D. A. Probst, R. E. Robinson and M. Yau, Tetrahedron Lett., 1999, 40, 4761; (b) for subsequent RCM approaches to 7-membered sultams see reference 5h and D. D. Long and A. P. Termin, Tetrahedron Lett., 2000, 41, 6743.
58. For the first synthesis of 6- and 7-membered sultams in solution using a RCM approach see: (a) P. R. Hanson, D. A. Probst, R. E. Robinson and M. Yau, Tetrahedron Lett., 1999, 40, 4761; (b) for subsequent RCM approaches to 7-membered sultams see reference 5h and D. D. Long and A. P. Termin, Tetrahedron Lett., 2000, 41, 6743.
59. 2) and GC quantification. (a) R. C. D. Brown and M. Fisher, Chem. Commun., 1999, 1547; (b) R. C. D. Brown, M. L. Fisher and L. J. Brown, Org. Biomol. Chem., 2003, 1, 2699.
60. 2) and GC quantification. (a) R. C. D. Brown and M. Fisher, Chem. Commun., 1999, 1547; (b) R. C. D. Brown, M. L. Fisher and L. J. Brown, Org. Biomol. Chem., 2003, 1, 2699.
61. (a) P. Deslongchamps, S. Lamothe and H. Lin, Can. J. Chem., 1987, 65, 1298;
62. (b) Y.-C. Xu, A. L. Roughton, R. Plante, S. Goldstein and P. Deslongchamps, Can. J. Chem., 1993, 71, 1152.
63. A. P. Krapcho, Synthesis, 1982, 805.
64. J. F. King and R. D. K. Harding, J. Am. Chem. Soc., 1976, 98, 3312.
65. M. A. Belous and I. Y. Postowskii, Zh. Obshch. Khtm., 1950, 20, 1701.
66. T. Tsuri, N. Haga, T. Matsui, S Kamata, H. Kakushi and K. Uchida, Chem. Pharm. Bull., 1992, 40, 75.
67. -1).
68. 2) and GC analysis of the cleaved alcohol.
69. -1 (37) based on 34 and 35.
70. The fact that some yields obtained were so high probably reflects an under estimation of the loading of the hydroxyl resins 34 and 35, although the RCM reaction must still be efficient process based on the loadings obtained for 36 and 37.
71. S. M. Dankwardt, D. B. Smith, J. A. Porco and C. H. Nguyen, Synlett, 1997, 854.
72. K. A. Beaver, A. C. Siegmund and K. L. Spear, Tetrahedron Lett., 1996, 37, 1145.
73. For some references describing methods to facilitate the removal of ruthenium impurities from metathesis products see: (a) H. D. Maynard and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 4137; (b) L. A. Paquette, J. D. Schloss, I. Efremov, F. Fabris, F. Gallou, J. Méndez-Andino and J. Yang, Org. Lett., 2000, 2, 1259; (c) Y. M. Ahn, K. Yang and G. I. Georg, Org. Lett., 2001, 3, 1411.
74. For some references describing methods to facilitate the removal of ruthenium impurities from metathesis products see: (a) H. D. Maynard and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 4137; (b) L. A. Paquette, J. D. Schloss, I. Efremov, F. Fabris, F. Gallou, J. Méndez-Andino and J. Yang, Org. Lett., 2000, 2, 1259; (c) Y. M. Ahn, K. Yang and G. I. Georg, Org. Lett., 2001, 3, 1411.
75. For some references describing methods to facilitate the removal of ruthenium impurities from metathesis products see: (a) H. D. Maynard and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 4137; (b) L. A. Paquette, J. D. Schloss, I. Efremov, F. Fabris, F. Gallou, J. Méndez-Andino and J. Yang, Org. Lett., 2000, 2, 1259; (c) Y. M. Ahn, K. Yang and G. I. Georg, Org. Lett., 2001, 3, 1411.
76. Examples of resin-bound metal alkylidene complexes that catalyse olefin metathesis have been reported previously: (a) S. T. Nguyen and R. H. Grubbs, J. Organomet. Chem., 1995, 497, 195; (b) M. Ahmed, A. G. M. Barrett, D. C. Braddock, S. M. Cramp and P. A. Procopiou, Tetrahedron Lett., 1999, 40, 8657; (c) M. Ahmed, T. Arnauld, A. G. M. Barrett, D. C. Braddock and P. A. Procopiou, Synlett, 2000, 1007.
77. Examples of resin-bound metal alkylidene complexes that catalyse olefin metathesis have been reported previously: (a) S. T. Nguyen and R. H. Grubbs, J. Organomet. Chem., 1995, 497, 195; (b) M. Ahmed, A. G. M. Barrett, D. C. Braddock, S. M. Cramp and P. A. Procopiou, Tetrahedron Lett., 1999, 40, 8657; (c) M. Ahmed, T. Arnauld, A. G. M. Barrett, D. C. Braddock and P. A. Procopiou, Synlett, 2000, 1007.
78. Examples of resin-bound metal alkylidene complexes that catalyse olefin metathesis have been reported previously: (a) S. T. Nguyen and R. H. Grubbs, J. Organomet. Chem., 1995, 497, 195; (b) M. Ahmed, A. G. M. Barrett, D. C. Braddock, S. M. Cramp and P. A. Procopiou, Tetrahedron Lett., 1999, 40, 8657; (c) M. Ahmed, T. Arnauld, A. G. M. Barrett, D. C. Braddock and P. A. Procopiou, Synlett, 2000, 1007.
79. R. M. Williams, M. R. Sabol, H. Kim and A. Kwast, J. Am. Chem. Soc., 1991, 113, 6621.