Total synthesis of the naturally occurring endothelin converting enzyme (ECE) inhibitor WS 75624 A

Synlett

Volumn , Issue 12, 2002, Pages 2089-2091

  Bach, Thorsten ^a   Heuser, Stefan ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cross coupling; Heterocycles; Palladium; Pyridines; Total synthesis

Indexed keywords

2,4 DIBROMOTHIAZOLE; 4 BROMOTHIAZOLE; ENDOTHELIN CONVERTING ENZYME INHIBITOR; THIAZOLE DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG; WS 75624A; ZINC DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DRUG SYNTHESIS;

EID: 0036456222     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35568     Document Type: Article

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15. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
16. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
17. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
18. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
19. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
20. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
21. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
22. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
23. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
24. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
25. Selected references on regioselective cross-coupling reactions of five-membered heterocycles: (a) Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845. (b) Minato, A.; Tamao, K.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 4017. (c) Karlsson, J. O.; Gronowitz, S.; Fried, T. J. Org. Chem. 1982, 47, 845. (d) Minato, K.; Suzuki, A.; Tamao, K.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511. (e) Carpita, A.; Rossi, R. Gazz. Chim. Ital. 1985, 115, 575. (f) Gronowitz, S.; Svensson, A. Isr. J. Chem. 1986, 27, 25. (g) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085. (h) Wang, D.; Haseltine, J. J. Heterocycl. Chem. 1994, 31, 1637. (i) Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247. (j) Pereira, R.; Iglesias, B.; de Lera, A. R. Tetrahedron 2001, 57, 7871. (k) Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
26. For general references on cross-coupling reactions of heterocycles, see: (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon Press: Oxford, 2000. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1999. (c) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998.
27. For general references on cross-coupling reactions of heterocycles, see: (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon Press: Oxford, 2000. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1999. (c) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998.
28. For general references on cross-coupling reactions of heterocycles, see: (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon Press: Oxford, 2000. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1999. (c) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998.
29. Reynaud, P.; Robba, M.; Moreau, R. C. Bull. Soc. Chim. Fr. 1962, 1735.
30. For regioselective Suzuki and Sonogashira cross-coupling reactions on substrate 2, see: (a) Wellmar, U.; Gronowitz, S.; H6rnfeldt, A.-B. J. Heterocycl Chem. 1995, 32, 1159. (b) Nicolaou, K. C.; He, Y.; Roschangar, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem. Int, Ed. 1998, 37, 84. (c) Nicolaou, K. C.; King, N. P,; Finlay, R. V.; He, Y.; Roschangar, F,; Vourloumis, D.; Vahlberg, H.; Sarabia, F.; Ninkovic, S.; Hepworth, D. Bioorg. Med. Chem. 1999, 7, 665. (d) See also: Langille N. F.; Dakin, L. A.; Panek, J. S. Org. Lett. 2002, 4, 2485.
31. For regioselective Suzuki and Sonogashira cross-coupling reactions on substrate 2, see: (a) Wellmar, U.; Gronowitz, S.; H6rnfeldt, A.-B. J. Heterocycl. Chem. 1995, 32, 1159. (b) Nicolaou, K. C.; He, Y.; Roschangar, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem. Int, Ed. 1998, 37, 84. (c) Nicolaou, K. C.; King, N. P,; Finlay, R. V.; He, Y.; Roschangar, F,; Vourloumis, D.; Vahlberg, H.; Sarabia, F.; Ninkovic, S.; Hepworth, D. Bioorg. Med. Chem. 1999, 7, 665. (d) See also: Langille N. F.; Dakin, L. A.; Panek, J. S. Org. Lett. 2002, 4, 2485.
32. For regioselective Suzuki and Sonogashira cross-coupling reactions on substrate 2, see: (a) Wellmar, U.; Gronowitz, S.; H6rnfeldt, A.-B. J. Heterocycl. Chem. 1995, 32, 1159. (b) Nicolaou, K. C.; He, Y.; Roschangar, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem. Int, Ed. 1998, 37, 84. (c) Nicolaou, K. C.; King, N. P,; Finlay, R. V.; He, Y.; Roschangar, F,; Vourloumis, D.; Vahlberg, H.; Sarabia, F.; Ninkovic, S.; Hepworth, D. Bioorg. Med. Chem. 1999, 7, 665. (d) See also: Langille N. F.; Dakin, L. A.; Panek, J. S. Org. Lett. 2002, 4, 2485.
33. For regioselective Suzuki and Sonogashira cross-coupling reactions on substrate 2, see: (a) Wellmar, U.; Gronowitz, S.; H6rnfeldt, A.-B. J. Heterocycl. Chem. 1995, 32, 1159. (b) Nicolaou, K. C.; He, Y.; Roschangar, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem. Int, Ed. 1998, 37, 84. (c) Nicolaou, K. C.; King, N. P,; Finlay, R. V.; He, Y.; Roschangar, F,; Vourloumis, D.; Vahlberg, H.; Sarabia, F.; Ninkovic, S.; Hepworth, D. Bioorg. Med. Chem. 1999, 7, 665. (d) See also: Langille N. F.; Dakin, L. A.; Panek, J. S. Org. Lett. 2002, 4, 2485.
34. Koch, V.; Schnatterer, S. Synthesis 1990, 497.
35. Compound 7 was obtained from methyl 5-bromopentanoate in 95% yield: Larsen, S. D.; Spilman, C. H.; Yagi, Y.; Dinh, D. M.; Hart, K. L.; Hess, G. F. J. Med. Chem. 1994, 37, 2343.
36. Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406.
37. 3) δ = 6.8, 7.1, 23.8, 29.9, 30.4, 33.7, 44.6, 73.2, 115.6, 124.2, 172.7.
38. The methods we tried included Pd(0)-catalyzed cross-coupling reactions with bis(pinacolato)diboron or hexamethyldistannane, halogen-metal exchange reactions and reductive metalations. For a review on this topic, see: Mongin, F.; Quéginer, G. Tetrahedron 2001, 57, 4059.
39. Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4623.
40. 3) δ = 6.5, 7.0, 24.0, 29.7, 30.4, 33.6, 44.5, 52.7, 56.1, 60.4, 73.0, 108.3, 120.1, 143.9, 145.8, 146.0, 149.8, 159.4, 165.5, 170.9.
41. Nicolaou, K. C.; Webber, S. E. Synthesis 1986, 453.