Ring closing metathesis in organic synthesis: Evolution of a high speed, solid phase method for the preparation of β-turn mimetics

Tetrahedron

Volumn 55, Issue 27, 1999, Pages 8189-8198

  Piscopio, Anthony D ^a,b   Miller, John F ^a,b,c   Koch, Kevin ^a,b  

^a AMGEN INC   (United States)

^b ARRAY BIOPHARMA INC   (United States)

^c GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033516498     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00300-2     Document Type: Article

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19. (a) Fu G.C.; Grubbs R.H. J. Am. Chem. Soc. 1993, 115, 3800-3801. (b) Grubbs R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995 28,446-452 and references cited therein. (c) Schmalz, H.-G. Agnew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein. (d) Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M.J. Am. Chem. Soc. 1990, 112, 3875-3886. (e) Bazan, G.C.; Schrock, R.R.; Cho, H.-N; Gibson, V.C. Macromolecules 1991, 24, 4495-4502. For recent applications of ring closing metathesis in natural products synthesis see: (f) Xu, Z. Johannes, C.W.; Salman, S.S.; Hoveyada, A.H. J. Am. Chem. Soc. 1996, 118, 10926-10927. (g) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008. (h) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193. (i) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyada, A. J. Am. Chem. Soc. 1995, 117, 2943-2944. (j) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (k) Nicolaou, K.C.; Winnsinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E.; Nature, 1997, 387, 268-262 and references cited therein.
20. (a) Fu G.C.; Grubbs R.H. J. Am. Chem. Soc. 1993, 115, 3800-3801. (b) Grubbs R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995 28,446-452 and references cited therein. (c) Schmalz, H.-G. Agnew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein. (d) Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M.J. Am. Chem. Soc. 1990, 112, 3875-3886. (e) Bazan, G.C.; Schrock, R.R.; Cho, H.-N; Gibson, V.C. Macromolecules 1991, 24, 4495-4502. For recent applications of ring closing metathesis in natural products synthesis see: (f) Xu, Z. Johannes, C.W.; Salman, S.S.; Hoveyada, A.H. J. Am. Chem. Soc. 1996, 118, 10926-10927. (g) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008. (h) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193. (i) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyada, A. J. Am. Chem. Soc. 1995, 117, 2943-2944. (j) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (k) Nicolaou, K.C.; Winnsinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E.; Nature, 1997, 387, 268-262 and references cited therein.
21. (a) Fu G.C.; Grubbs R.H. J. Am. Chem. Soc. 1993, 115, 3800-3801. (b) Grubbs R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995 28,446-452 and references cited therein. (c) Schmalz, H.-G. Agnew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein. (d) Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M.J. Am. Chem. Soc. 1990, 112, 3875-3886. (e) Bazan, G.C.; Schrock, R.R.; Cho, H.-N; Gibson, V.C. Macromolecules 1991, 24, 4495-4502. For recent applications of ring closing metathesis in natural products synthesis see: (f) Xu, Z. Johannes, C.W.; Salman, S.S.; Hoveyada, A.H. J. Am. Chem. Soc. 1996, 118, 10926-10927. (g) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008. (h) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193. (i) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyada, A. J. Am. Chem. Soc. 1995, 117, 2943-2944. (j) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (k) Nicolaou, K.C.; Winnsinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E.; Nature, 1997, 387, 268-262 and references cited therein.
22. (a) Fu G.C.; Grubbs R.H. J. Am. Chem. Soc. 1993, 115, 3800-3801. (b) Grubbs R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995 28,446-452 and references cited therein. (c) Schmalz, H.-G. Agnew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein. (d) Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M.J. Am. Chem. Soc. 1990, 112, 3875-3886. (e) Bazan, G.C.; Schrock, R.R.; Cho, H.-N; Gibson, V.C. Macromolecules 1991, 24, 4495-4502. For recent applications of ring closing metathesis in natural products synthesis see: (f) Xu, Z. Johannes, C.W.; Salman, S.S.; Hoveyada, A.H. J. Am. Chem. Soc. 1996, 118, 10926-10927. (g) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008. (h) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193. (i) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyada, A. J. Am. Chem. Soc. 1995, 117, 2943-2944. (j) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (k) Nicolaou, K.C.; Winnsinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E.; Nature, 1997, 387, 268-262 and references cited therein.
23. (a) Fu G.C.; Grubbs R.H. J. Am. Chem. Soc. 1993, 115, 3800-3801. (b) Grubbs R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995 28,446-452 and references cited therein. (c) Schmalz, H.-G. Agnew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein. (d) Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M.J. Am. Chem. Soc. 1990, 112, 3875-3886. (e) Bazan, G.C.; Schrock, R.R.; Cho, H.-N; Gibson, V.C. Macromolecules 1991, 24, 4495-4502. For recent applications of ring closing metathesis in natural products synthesis see: (f) Xu, Z. Johannes, C.W.; Salman, S.S.; Hoveyada, A.H. J. Am. Chem. Soc. 1996, 118, 10926-10927. (g) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008. (h) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193. (i) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyada, A. J. Am. Chem. Soc. 1995, 117, 2943-2944. (j) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (k) Nicolaou, K.C.; Winnsinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E.; Nature, 1997, 387, 268-262 and references cited therein.
24. (a) Fu G.C.; Grubbs R.H. J. Am. Chem. Soc. 1993, 115, 3800-3801. (b) Grubbs R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995 28,446-452 and references cited therein. (c) Schmalz, H.-G. Agnew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein. (d) Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M.J. Am. Chem. Soc. 1990, 112, 3875-3886. (e) Bazan, G.C.; Schrock, R.R.; Cho, H.-N; Gibson, V.C. Macromolecules 1991, 24, 4495-4502. For recent applications of ring closing metathesis in natural products synthesis see: (f) Xu, Z. Johannes, C.W.; Salman, S.S.; Hoveyada, A.H. J. Am. Chem. Soc. 1996, 118, 10926-10927. (g) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008. (h) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193. (i) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyada, A. J. Am. Chem. Soc. 1995, 117, 2943-2944. (j) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (k) Nicolaou, K.C.; Winnsinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E.; Nature, 1997, 387, 268-262 and references cited therein.
25. (a) Fu G.C.; Grubbs R.H. J. Am. Chem. Soc. 1993, 115, 3800-3801. (b) Grubbs R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995 28,446-452 and references cited therein. (c) Schmalz, H.-G. Agnew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein. (d) Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M.J. Am. Chem. Soc. 1990, 112, 3875-3886. (e) Bazan, G.C.; Schrock, R.R.; Cho, H.-N; Gibson, V.C. Macromolecules 1991, 24, 4495-4502. For recent applications of ring closing metathesis in natural products synthesis see: (f) Xu, Z. Johannes, C.W.; Salman, S.S.; Hoveyada, A.H. J. Am. Chem. Soc. 1996, 118, 10926-10927. (g) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008. (h) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193. (i) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyada, A. J. Am. Chem. Soc. 1995, 117, 2943-2944. (j) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (k) Nicolaou, K.C.; Winnsinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E.; Nature, 1997, 387, 268-262 and references cited therein.
26. (a) Fu G.C.; Grubbs R.H. J. Am. Chem. Soc. 1993, 115, 3800-3801. (b) Grubbs R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995 28,446-452 and references cited therein. (c) Schmalz, H.-G. Agnew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein. (d) Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M.J. Am. Chem. Soc. 1990, 112, 3875-3886. (e) Bazan, G.C.; Schrock, R.R.; Cho, H.-N; Gibson, V.C. Macromolecules 1991, 24, 4495-4502. For recent applications of ring closing metathesis in natural products synthesis see: (f) Xu, Z. Johannes, C.W.; Salman, S.S.; Hoveyada, A.H. J. Am. Chem. Soc. 1996, 118, 10926-10927. (g) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008. (h) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193. (i) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyada, A. J. Am. Chem. Soc. 1995, 117, 2943-2944. (j) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (k) Nicolaou, K.C.; Winnsinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E.; Nature, 1997, 387, 268-262 and references cited therein.
27. (a) Fu G.C.; Grubbs R.H. J. Am. Chem. Soc. 1993, 115, 3800-3801. (b) Grubbs R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995 28,446-452 and references cited therein. (c) Schmalz, H.-G. Agnew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein. (d) Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M.J. Am. Chem. Soc. 1990, 112, 3875-3886. (e) Bazan, G.C.; Schrock, R.R.; Cho, H.-N; Gibson, V.C. Macromolecules 1991, 24, 4495-4502. For recent applications of ring closing metathesis in natural products synthesis see: (f) Xu, Z. Johannes, C.W.; Salman, S.S.; Hoveyada, A.H. J. Am. Chem. Soc. 1996, 118, 10926-10927. (g) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008. (h) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193. (i) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyada, A. J. Am. Chem. Soc. 1995, 117, 2943-2944. (j) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008. (k) Nicolaou, K.C.; Winnsinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E.; Nature, 1997, 387, 268-262 and references cited therein.
28. (a) Piscopio A.D.; Miller, J.F.; Koch, K. Tetrahedron Letters 1998, 39, 2667-2670. (b) Piscopio, A.D.; Miller, J.F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143-7146. For other solid phase applications of ring closing meteathesis see: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614. (b) Schuster, M.; Pernerstorfer, S. B. Angew. Chem. 1996, 108, 2111-2112. (c) van Maarseveen, Jan H.; den Hartog, Jack A. J.; Engelen, Victor; Finner, Emil; Visser, Geb; Kruse, Chris G. Tetrahedron Lett. 1996, 37, 8249-8252. (d) see reference 9k.
29. (a) Piscopio A.D.; Miller, J.F.; Koch, K. Tetrahedron Letters 1998, 39, 2667-2670. (b) Piscopio, A.D.; Miller, J.F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143-7146. For other solid phase applications of ring closing meteathesis see: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614. (b) Schuster, M.; Pernerstorfer, S. B. Angew. Chem. 1996, 108, 2111-2112. (c) van Maarseveen, Jan H.; den Hartog, Jack A. J.; Engelen, Victor; Finner, Emil; Visser, Geb; Kruse, Chris G. Tetrahedron Lett. 1996, 37, 8249-8252. (d) see reference 9k.
30. (a) Piscopio A.D.; Miller, J.F.; Koch, K. Tetrahedron Letters 1998, 39, 2667-2670. (b) Piscopio, A.D.; Miller, J.F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143-7146. For other solid phase applications of ring closing meteathesis see: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614. (b) Schuster, M.; Pernerstorfer, S. B. Angew. Chem. 1996, 108, 2111-2112. (c) van Maarseveen, Jan H.; den Hartog, Jack A. J.; Engelen, Victor; Finner, Emil; Visser, Geb; Kruse, Chris G. Tetrahedron Lett. 1996, 37, 8249-8252. (d) see reference 9k.
31. (a) Piscopio A.D.; Miller, J.F.; Koch, K. Tetrahedron Letters 1998, 39, 2667-2670. (b) Piscopio, A.D.; Miller, J.F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143-7146. For other solid phase applications of ring closing meteathesis see: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614. (b) Schuster, M.; Pernerstorfer, S. B. Angew. Chem. 1996, 108, 2111-2112. (c) van Maarseveen, Jan H.; den Hartog, Jack A. J.; Engelen, Victor; Finner, Emil; Visser, Geb; Kruse, Chris G. Tetrahedron Lett. 1996, 37, 8249-8252. (d) see reference 9k.
32. (a) Piscopio A.D.; Miller, J.F.; Koch, K. Tetrahedron Letters 1998, 39, 2667-2670. (b) Piscopio, A.D.; Miller, J.F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143-7146. For other solid phase applications of ring closing meteathesis see: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614. (b) Schuster, M.; Pernerstorfer, S. B. Angew. Chem. 1996, 108, 2111-2112. (c) van Maarseveen, Jan H.; den Hartog, Jack A. J.; Engelen, Victor; Finner, Emil; Visser, Geb; Kruse, Chris G. Tetrahedron Lett. 1996, 37, 8249-8252. (d) see reference 9k.
33. (a) Piscopio A.D.; Miller, J.F.; Koch, K. Tetrahedron Letters 1998, 39, 2667-2670. (b) Piscopio, A.D.; Miller, J.F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143-7146. For other solid phase applications of ring closing meteathesis see: (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614. (b) Schuster, M.; Pernerstorfer, S. B. Angew. Chem. 1996, 108, 2111-2112. (c) van Maarseveen, Jan H.; den Hartog, Jack A. J.; Engelen, Victor; Finner, Emil; Visser, Geb; Kruse, Chris G. Tetrahedron Lett. 1996, 37, 8249-8252. (d) see reference 9k.
34. For pioneering work in the area of polymer supported synthesis see: (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149. (b) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 3045.
35. For pioneering work in the area of polymer supported synthesis see: (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149. (b) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 3045.
36. Solid phase synthesis reviews: (a) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gorden, E. M. J. Med. Chem. 1994, 37, 1233-1251. (d) Gorden, E. M.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401. (e) Moos, W.H.; Green, G. D.; Pavia, M. R. Annu. Report Med. Chem. 1993, 28, 315-324. (f) Leznoff, C. C. Acc. Chem. Res. 1978, 11 327-333. (g) Crowley, J.I.; Rapaport, H. Acc. Chem. Res. 1976, 9, 135-144.
37. Solid phase synthesis reviews: (a) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gorden, E. M. J. Med. Chem. 1994, 37, 1233-1251. (d) Gorden, E. M.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401. (e) Moos, W.H.; Green, G. D.; Pavia, M. R. Annu. Report Med. Chem. 1993, 28, 315-324. (f) Leznoff, C. C. Acc. Chem. Res. 1978, 11 327-333. (g) Crowley, J.I.; Rapaport, H. Acc. Chem. Res. 1976, 9, 135-144.
38. Solid phase synthesis reviews: (a) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gorden, E. M. J. Med. Chem. 1994, 37, 1233-1251. (d) Gorden, E. M.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401. (e) Moos, W.H.; Green, G. D.; Pavia, M. R. Annu. Report Med. Chem. 1993, 28, 315-324. (f) Leznoff, C. C. Acc. Chem. Res. 1978, 11 327-333. (g) Crowley, J.I.; Rapaport, H. Acc. Chem. Res. 1976, 9, 135-144.
39. Solid phase synthesis reviews: (a) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gorden, E. M. J. Med. Chem. 1994, 37, 1233-1251. (d) Gorden, E. M.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401. (e) Moos, W.H.; Green, G. D.; Pavia, M. R. Annu. Report Med. Chem. 1993, 28, 315-324. (f) Leznoff, C. C. Acc. Chem. Res. 1978, 11 327-333. (g) Crowley, J.I.; Rapaport, H. Acc. Chem. Res. 1976, 9, 135-144.
40. Solid phase synthesis reviews: (a) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gorden, E. M. J. Med. Chem. 1994, 37, 1233-1251. (d) Gorden, E. M.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401. (e) Moos, W.H.; Green, G. D.; Pavia, M. R. Annu. Report Med. Chem. 1993, 28, 315-324. (f) Leznoff, C. C. Acc. Chem. Res. 1978, 11 327-333. (g) Crowley, J.I.; Rapaport, H. Acc. Chem. Res. 1976, 9, 135-144.
41. Solid phase synthesis reviews: (a) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gorden, E. M. J. Med. Chem. 1994, 37, 1233-1251. (d) Gorden, E. M.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401. (e) Moos, W.H.; Green, G. D.; Pavia, M. R. Annu. Report Med. Chem. 1993, 28, 315-324. (f) Leznoff, C. C. Acc. Chem. Res. 1978, 11 327-333. (g) Crowley, J.I.; Rapaport, H. Acc. Chem. Res. 1976, 9, 135-144.
42. Solid phase synthesis reviews: (a) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (c) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gorden, E. M. J. Med. Chem. 1994, 37, 1233-1251. (d) Gorden, E. M.; Barret, R. W.; Dower, W. J.; Foder, S. P.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401. (e) Moos, W.H.; Green, G. D.; Pavia, M. R. Annu. Report Med. Chem. 1993, 28, 315-324. (f) Leznoff, C. C. Acc. Chem. Res. 1978, 11 327-333. (g) Crowley, J.I.; Rapaport, H. Acc. Chem. Res. 1976, 9, 135-144.
43. For use of traceless linkers see: (a) Gayo, L.M.; Suto, M.J. Tetrahedron Lett. 1997, 38, 211-214. (b) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett., 1996, 37, 6491-6494. (c) Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007. (d) Chenara, B.; Finkelstein, J. A.; Verber, D.F. J. Am. Chem. Soc. 1995, 117, 11999-12000.
44. For use of traceless linkers see: (a) Gayo, L.M.; Suto, M.J. Tetrahedron Lett. 1997, 38, 211-214. (b) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett., 1996, 37, 6491-6494. (c) Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007. (d) Chenara, B.; Finkelstein, J. A.; Verber, D.F. J. Am. Chem. Soc. 1995, 117, 11999-12000.
45. For use of traceless linkers see: (a) Gayo, L.M.; Suto, M.J. Tetrahedron Lett. 1997, 38, 211-214. (b) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett., 1996, 37, 6491-6494. (c) Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007. (d) Chenara, B.; Finkelstein, J. A.; Verber, D.F. J. Am. Chem. Soc. 1995, 117, 11999-12000.
46. For use of traceless linkers see: (a) Gayo, L.M.; Suto, M.J. Tetrahedron Lett. 1997, 38, 211-214. (b) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett., 1996, 37, 6491-6494. (c) Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007. (d) Chenara, B.; Finkelstein, J. A.; Verber, D.F. J. Am. Chem. Soc. 1995, 117, 11999-12000.
47. For use of cyclative cleavage protocol see: (a) Mayer, J. P.; Zhang, J.; Bjergarde, K.; Lenz, D. M.; Gaudino, J. J. Tetrahedron Lett., 1996, 37, 8081-8084. (b) Smith, A. L.; Thomson, C. G.; Leeson, Paul, D. Bioorg. Med. Chem. Lett. 1996, 6, 1483-1486. (c) Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett., 1994, 35, 8915-8918. (d) Dewitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909-6913. (e) Beebe, X.; Schore, N. E.; Kurth, M. J. J. Am. Chem. Soc. 1992, 114, 10061-10062.
48. For use of cyclative cleavage protocol see: (a) Mayer, J. P.; Zhang, J.; Bjergarde, K.; Lenz, D. M.; Gaudino, J. J. Tetrahedron Lett., 1996, 37, 8081-8084. (b) Smith, A. L.; Thomson, C. G.; Leeson, Paul, D. Bioorg. Med. Chem. Lett. 1996, 6, 1483-1486. (c) Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett., 1994, 35, 8915-8918. (d) Dewitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909-6913. (e) Beebe, X.; Schore, N. E.; Kurth, M. J. J. Am. Chem. Soc. 1992, 114, 10061-10062.
49. For use of cyclative cleavage protocol see: (a) Mayer, J. P.; Zhang, J.; Bjergarde, K.; Lenz, D. M.; Gaudino, J. J. Tetrahedron Lett., 1996, 37, 8081-8084. (b) Smith, A. L.; Thomson, C. G.; Leeson, Paul, D. Bioorg. Med. Chem. Lett. 1996, 6, 1483-1486. (c) Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett., 1994, 35, 8915-8918. (d) Dewitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909-6913. (e) Beebe, X.; Schore, N. E.; Kurth, M. J. J. Am. Chem. Soc. 1992, 114, 10061-10062.
50. For use of cyclative cleavage protocol see: (a) Mayer, J. P.; Zhang, J.; Bjergarde, K.; Lenz, D. M.; Gaudino, J. J. Tetrahedron Lett., 1996, 37, 8081-8084. (b) Smith, A. L.; Thomson, C. G.; Leeson, Paul, D. Bioorg. Med. Chem. Lett. 1996, 6, 1483-1486. (c) Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett., 1994, 35, 8915-8918. (d) Dewitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909-6913. (e) Beebe, X.; Schore, N. E.; Kurth, M. J. J. Am. Chem. Soc. 1992, 114, 10061-10062.
51. For use of cyclative cleavage protocol see: (a) Mayer, J. P.; Zhang, J.; Bjergarde, K.; Lenz, D. M.; Gaudino, J. J. Tetrahedron Lett., 1996, 37, 8081-8084. (b) Smith, A. L.; Thomson, C. G.; Leeson, Paul, D. Bioorg. Med. Chem. Lett. 1996, 6, 1483-1486. (c) Moon, H.-S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett., 1994, 35, 8915-8918. (d) Dewitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909-6913. (e) Beebe, X.; Schore, N. E.; Kurth, M. J. J. Am. Chem. Soc. 1992, 114, 10061-10062.
52. Bazan, G.C.; Khosvravi, E.; Schrock, R.R.; Feast, W.J.; Gibson, V.C.; O'Regan, J.K.; Thomas, J.K.; Davis, W.M. J. Am. Chem. Soc. 1990, 112, 8378-8387 and references cited therein.
53. Frechet, J. M.; Schuerch, C. J. J. Am. Chem. Soc. 1971, 93, 492-496.
54. (a) Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831-5834. (b) Cheung, M.; Jow, C.-K.; Fukuyama, T. Book of Abstracts, 211th ACS Meeting, New Orleans, La. March 24-28, 1996, ORG-215 ACS, Washington D.C.
55. (a) Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831-5834. (b) Cheung, M.; Jow, C.-K.; Fukuyama, T. Book of Abstracts, 211th ACS Meeting, New Orleans, La. March 24-28, 1996, ORG-215 ACS, Washington D.C.
56. Mitsunobu, O. Synthesis, 1981, 1-28.
57. Based on recovered N-(n-Butyl)-2,4-dinitroaniline from sulfonamide removal with n-butylamine (assumes quantitative cleavage): see reference 18.
58. 6 (5-10%) when HATU was used as the coupling reagent despite rigorous washing of the resin, and tricyclohexylphosphine oxide < 5%.
59. 6 (5-10%) when HATU was used as the coupling reagent despite rigorous washing of the resin, and tricyclohexylphosphine oxide < 5%.
60. (S)-Allyl glycine and (S)-methyl-2-hydroxy-3-phenyl propionate were used and a single diastereomeric product (8) was obtained, presumably with inversion of configuration during the loading step.
61. The amount of recovered 11 indicated a quantitative conversion of 1 to 10 and I.R. analysis in the conversion of resin 10 to resin 13 revealed a complete disappearance of the characteristic (t-Boc) carbonyl stretch.
62. For a comprehensive review see: Balkenhohl, F.; Bussche-Hunnefeld, C. v.d.; Lansky, A; Zechel, C. Angew. Chem. Int. Ed. Eng. 1996, 35, 2288-2337.
63. Ugi, I; Lohberger, S,; Karl, R. In Comprehensive Organic Synthesis; Trost, B.M., Flemming, I., Eds.; Pergamon: New York, 1991; Vol. 2; pp 1083-1109.
64. (a) Tempest, P.A.; Armstrong, R.W. J. Am. Chem. Soc. 1997, 119, 7607-7608 (b) Armstrong, R.W.; Combs, A.P.; Tempest, P.A.; Brown, S.D.; Keating, T.A.; Acc. Chem. Res. 1996, 29, 123-131.
65. (a) Tempest, P.A.; Armstrong, R.W. J. Am. Chem. Soc. 1997, 119, 7607-7608 (b) Armstrong, R.W.; Combs, A.P.; Tempest, P.A.; Brown, S.D.; Keating, T.A.; Acc. Chem. Res. 1996, 29, 123-131.
66. Based on chemical yields obtained using analogous substrates in solution phase.
67. Ugi, I; Fetzer, U; Eholzer, U; Knupfer, H; Offerman, K. Angew. Chem. Int. Ed. Engl. 1965, 4, 472-484.
68. Based on HPLC-mass spectral analysis.