Regioselective C-C bond formation reactions on 2,3-dibromo- and 2,3,5-tribromobenzofuran as an access to multiply substituted benzofurans. Total syntheses of eupomatenoids 3, 4, 5, 6, and 15

Synthesis

Volumn , Issue 6, 2003, Pages 925-939

  Bach, Thorsten ^a   Bartels, Marc ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Benzofurans; Cross coupling; Natural products; Oxygen heterocycles; Regioselectivity

Indexed keywords

REGIOSELECTIVITY;

CATALYSTS; CHEMICAL BONDS; FURAN RESINS; PALLADIUM;

SYNTHESIS (CHEMICAL);

(3 BROMOBENZOFURAN 2 YLETHYNYL)TRIMETHYLSILANE; 1 (3 BROMOBENZOFURAN 2 YL) 3 METHYLPENT 1 YN 3 OL; 2 (4 METHOXYPHENYL) 3 METHYL 5 PROP 1 ENYLBENZOFURAN; 2,3 DIBROMOBENZOFURAN; 2,3,5 TRIBROMOBENZOFURAN; 3 (3 BROMOBENZOFURAN 2 YL)PROP 2 YN 1 OL; 3 BROMO 2 (3 METHOXYPROP 1 YNYL)BENZOFURAN; 3 BROMO 2 (3,3 DIMETHYLBUT 1 YNYL)BENZOFURAN; 3 BROMO 2 (4 METHOXYPHENYL)BENZOFURAN; 3 BROMO 2 PHENYLETHYNYL BENZOFURAN; 3,5 DIBROMO 2 (3 METHOXYPROP 1 YNYL)BENZOFURAN; 3,5 DIBROMO 2 (3,3 DIMETHYLBUT 1 YNYL)BENZOFURAN; 3,5 DIBROMO 2 (3,4 DIMETHOXYPHENYL)BENZOFURAN; 3,5 DIBROMO 2 (4 METHOXYPHENYL)BENZOFURAN; 3,5 DIBROMO 2 PHENYLETHYNYLBENZOFURAN; 4 (3 BROMOBENZOFURAN 2 YL)BUT 3 YN 1 OL; 4 (3 BROMOBENZOFURAN 2 YL)BUT 3 YN 2 OL; 4 (3,5 DIBROMOBENZOFURAN 2 YL)BUT 3 YN 1 OL; 5 (3 METHYL 5 PROP 1 ENYLBENZOFURAN 2 YL)BENZO[1,3]DIOXOLE; 5 (3,5 DIBROMOBENZOFURAN 2 YL)BENZO[1,3]DIOXOLE; BROMINE; CARBON; CHEMICAL COMPOUND; FURAN DERIVATIVE; HALOGEN; METAL; PALLADIUM; SILANE DERIVATIVE; TERT BUTYL[4 (3,5 DIBROMOBENZOFURAN 2 YL) 2 METHOXYPHENOXYLDIMETHYL SILANE; TERT BUTYL[4 (3,5 DIBROMOBENZOFURAN 2 YL)PHENOXY]DIMETHYLSILANE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038367727     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (86)

1. Reviews: (a) Dell, C. B. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations; Thomas, E. J., Ed.; Thieme: Stuttgart, 2001, Vol. 10, 11-86.
2. (b) Röhrkasten, R.; Konrad, M. In Houben-Weyl, Methoden der Organischen Chemie; Kreher, R. P., Ed.; Thieme: Stuttgart, 1994.
3. (c) Benassi R., Heany H., Ahn J. S., Friedrichsen W., Keay B. A., Dibble P. W.; In Comprehensive Heterocyclic Chemistry. 11; Katritzky A. R., Rees C. W; Scriven E. F. V., Bird C. W.; Pergamon: Oxford, 1996; Vol. 2, 259-436.
4. (d) Dean F. M., Sargent M. V., Donnelly D. M. X., Meegan M. J.; In Comprehensive Heterocyclic Chemistry.; Katritzky A. R., Rees C. W., Bird C. W., Cheeseman G. W. H.; Pergamon: Oxford, 1984; Vol. 4, 531-712.
5. (e) Cagniant F., Cagniant D.; Adv. Heterocycl. Chem.; 1975, 18: 337.
6. (f) Mustafa, A. In The Chemistry of Heterocyclic Compounds, Vol. 29; Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1974, 1-142.
7. Reviews: (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon Press: Oxford, 2000.
8. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic; Springer: Berlin, 1999.
9. (c) Diederich, F.; Stang, P. J. Metalcatalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998.
10. (d) Collins, I. J. Chem. Soc., Perkin Trans. 1 2000, 2845.
11. (e) Collins, I. J. Chem. Soc., Perkin Trans. 1 2002, 1921.
12. (a) Eberbach, W.; Laber, N.; Bussenius, J.; Fritz, H.; Rihs, G. Chem. Ber. 1993, 126, 975.
13. (b) Hudkins, R. L.; Diebold, J. L.; Marsh, F. D. J. Org. Chem. 1995, 60, 6218.
14. (c) Negishi, E.-I.; Xu, C.; Tan, Z.; Kotora, M. Heterocycles 1997, 46, 209.
15. (d) Clough, J. M.; Mann, I. S.; Widdowson, D. A. Tetrahedron Lett. 1987, 28, 2645.
16. (a) Judd, D. B.; Dowle, M. D.; Middlemiss, D.; Scopes, D. I. C.; Ross, B. C.; Jack, T. I.; Pass, M.; Tranquillini, E.; Hobson, J. E.; Panchal, T. A.; Stuart, P. G.; Paton, J. M. S.; Hubbard, T.; Hilditch, A.; Drew, G. M.; Robertson, M. J.; Clark, K. L.; Travers, A.; Hunt, A. A. E.; Polley, J.; Eddershaw, P. J.; Bayliss, M. K.; Manchee, G. R.; Donnelly, M. D.; Walker, D. G.; Richards, S. A. J. Med. Chem. 1994, 37, 3108.
17. (b) Nordvall, G.; Sundquist, S.; Johansson, G.; Glas, G.; Nilvebrant, L.; Hacksell, U. J. Med. Chem. 1996, 39, 3269.
18. (c) Banwell, M. G.; Flynn, B. L.; Willis, A. C.; Hamel, E. Aust. J. Chem. 1999, 52, 767.
19. (d) Deprets, S.; Kirsch, G. Eur. J. Org. Chem. 2000, 1353.
20. (e) Deprets, S.; Kirsch, G. Heterocycl. Commun. 2001, 7, 421.
21. (f) Zhang, Y.; Herndon, J. W. J. Org. Chem. 2002, 67, 4177.
22. (a) Wadsworth, A. H.; Mitchell, H. A.; Fellows, I.; Sutherland, D. R. J. Labelled Compd. Radiopharm. 1996, 38, 863.
23. (b) Glase, S. A.; Akunne, H. C.; Heffner, T. G.; Jaen, J. C.; MacKenzie, R. G.; Meltzer, L. T.; Pugsley, T. A.; Smith, S. J.; Wise, L. D. J. Med. Chem. 1996, 39, 3179.
24. (c) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969. (d) Yoo, S.-E.; Lee, S.-H.; Kim, S.-K.; Lee, S.-H. Bioorg. Med. Chem. 1997, 5, 445.
25. (d) Yoo, S.-E.; Lee, S.-H.; Kim, S.-K.; Lee, S.-H. Bioorg. Med. Chem. 1997, 5, 445.
26. (e) Kelly, T. R.; Szabados, A.; Lee, Y.-J. J. Org. Chem. 1997, 62, 428.
27. (f) Soós, T.; Timári, G.; Hajós, G. Tetrahedron Lett. 1999, 40, 8607.
28. (g) Kratky, P.; Haslinger, U.; Widhalm, M. Mh. Chem. 1998, 129, 1319.
29. (h) Kerrigan, F.; Martin, C.; Thomas, G. H. Tetrahedron Lett. 1998, 39, 2219.
30. (a) Torrado, A.; López, S.; Alvarez, R.; de Lera, A. R. Synthesis 1995, 285.
31. (b) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413.
32. (c) Philippo, C. M. G.; Mougenot, P.; Braun, A.; Defosse, G.; Auboussier, S.; Bovy, P. R. Synthesis 2000, 127.
33. (d) Sessler, J. L. Wang, R. J. Org. Chem. 1998, 63, 4079.
34. (e) Peglion, J.-L.; Goument, B.; Despaux, N.; Charlot, V.; Giraud, H.; Nisole, C.; Newman-Tancredi, A.; Dekeyne, A.; Bertrand, M.; Genissel, P.; Millan, M. J. J. Med. Chem. 2002, 45, 165.
35. (f) Rossi, R.; Bellina, F.; Ciucci, D.; Carpita, A.; Fanelli, C. Tetrahedron 1998, 54, 7595.
36. (g) Cram, D. J.; Dicker, I. B.; Lauer, M.; Knobler, C. B.; Trueblood, K. N. J. Am. Chem. Soc. 1984, 106, 7150.
37. (h) Cram, D. J.; DeGrandpre, M.; Knobler, C. B.; Trueblood, K. N. J. Am. Chem. Soc. 1984, 106, 3286.
38. Werner, A.; Friedrichsen, W. Synth. Commun. 1993, 23, 2973.
39. Benincori, T.; Brenna, E.; Sannicolo, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. J. Org. Chem. 1996, 61, 6244.
40. (a) Dann, O.; Fick, H.; Pietzner, B.; Walkenhorst, E.; Fernbach, R.; Zeh, D. Justus Liebigs Ann. Chem. 1975, 160.
41. (b) Dann, O.; Char, H.; Griessmeier, H. Liebigs Ann. Chem. 1982, 1836.
42. (c) Bohlmann, F.; Fritz, G. Tetrahedron 1982, 38, 1431.
43. (d) Cross, P.E.; Dickinson, R. P.; Parry, M. J.; Randall, M. J. J. Med. Chem. 1986, 29, 1643.
44. (e) Dow, R. L.; Bechle, B. M.; Chou, T. T.; Clark, D. A.; Hulin, B.; Stevenson, R. W. J. Med. Chem. 1991, 34, 1538.
45. (f) Sall, D. J.; Arfsten, A. E.; Bastian, J. A.; Denney, M. L.; Harms, C. S.; McCowan, J. R.; Morin, J. M. Jr.; Rose, J. W.; Scarborough, R. M.; Smyth, M. S.; Um, S. L.; Utterback, B. G.; Vasileff, R. T.; Wikel, J. H.; Wyss, V. L.; Jakubowski, J. A. J. Med. Chem. 1997, 40, 2843.
46. (g) Tashiro, M.; Yoshiya, H.; Fukata, G, J. Org. Chem. 1982, 47, 4425.
47. (h) Hellwinkel, D.; Kistenmacher, T. Liebigs Ann. Chem. 1989, 945.
48. Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988.
49. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432.
50. LaBrenz, S. R.; Bekele, H.; Kelly, J. W. Tetrahedron 1998, 54, 8671.
51. (a) Murray, R. D. H.; Zeghdi, S. Phytochemistry 1989, 28, 227.
52. (b) Bekele, H.; Nesloney, C. L.; McWilliams, K. W.; Zacharias, N. M.; Chitnumsub, P.; Kelly, J. W. J. Org. Chem. 1997, 62, 2259.
53. (a) Cugnon de Sevricourt, M.; Robba, M. Bull. Soc. Chim. Fr. 1977, 139.
54. (b) Cugnon de Sevricourt, M.; Robba, M. Bull. Chim. Soc. Fr. 1977, 142.
55. Bosold, F.; Zulauf, P.; Marsch, M.; Harms, K.; Lohrenz, J.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1455; Angew. Chem. 1991, 103, 1497 and references cited therein.
56. Bosold, F.; Zulauf, P.; Marsch, M.; Harms, K.; Lohrenz, J.; Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1455; Angew. Chem. 1991, 103, 1497 and references cited therein.
57. Bussenius, J.; Laber, N.; Müller, T.; Eberbach, W. Chem. Ber. 1994, 127, 247.
58. (a) Bach, T.; Krüger, L. Tetrahedron Lett. 1998, 39, 1729.
59. (b) Bach, T.; Krüger, L. Synlett 1998, 1185.
60. (c) Bach, T.; Krüger, L. Eur. J. Org. Chem. 1999, 2045.
61. (a) Bach, T.; Heuser, S. Tetrahedron Lett. 2000, 41, 1707.
62. (b) Bach, T.; Heuser, S. Angew. Chem. Int. Ed. 2001, 40, 3184; Angew. Chem. 2001, 113, 3283.
63. (b) Bach, T.; Heuser, S. Angew. Chem. Int. Ed. 2001, 40, 3184; Angew. Chem. 2001, 113, 3283.
64. (c) Bach, T.; Heuser, S. J. Org. Chem. 2002, 67, 5789. (d) Bach, T.; Heuser, S. Chem.-Eur. J. 2002, 8, 5585.
65. (d) Bach, T.; Heuser, S. Chem.-Eur. J. 2002, 8, 5585.
66. (e) Bach, T.; Heuser, S. Synlett 2002, 2089.
67. (a) Bowden, B. F.; Ritchie, E.; Taylor, W. C. Austr. J. Chem. 1972, 25, 2659.
68. (b) Picker, K.; Ritchie, E.; Taylor, W. C. Austr. J. Chem. 1973, 26, 1111.
69. (c) Read, R. W.; Taylor, W. C. Austr. J. Chem. 1979, 32, 2317.
70. (d) Carroll, A. R.; Taylor, W. C. Austr. J. Chem. 1991, 44, 1615.
71. (e) Carroll, A. R.; Taylor, W. C. Austr. J. Chem. 1991, 44, 1627; and referenes cited therein.
72. Previous syntheses of eupomatenoids: (a) Ahmed, R.; Stevenson, R. Phytochemistry 1975, 14, 2710. (b) McKittrick, B. A.; Stevenson, R. J. Chem. Soc., Perkin Trans. 1 1983, 475. (c) Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297. (d) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969.
73. Previous syntheses of eupomatenoids: (a) Ahmed, R.; Stevenson, R. Phytochemistry 1975, 14, 2710. (b) McKittrick, B. A.; Stevenson, R. J. Chem. Soc., Perkin Trans. 1 1983, 475. (c) Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297. (d) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969.
74. Previous syntheses of eupomatenoids: (a) Ahmed, R.; Stevenson, R. Phytochemistry 1975, 14, 2710. (b) McKittrick, B. A.; Stevenson, R. J. Chem. Soc., Perkin Trans. 1 1983, 475. (c) Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297. (d) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969.
75. Previous syntheses of eupomatenoids: (a) Ahmed, R.; Stevenson, R. Phytochemistry 1975, 14, 2710. (b) McKittrick, B. A.; Stevenson, R. J. Chem. Soc., Perkin Trans. 1 1983, 475. (c) Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297. (d) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969.
76. Preliminary communications: (a) Bach, T.; Bartels, M. Synlett 2001, 1284. (b) Bach, T.; Bartels, M. Tetrahedron Lett. 2002, 43, 9125.
77. Preliminary communications: (a) Bach, T.; Bartels, M. Synlett 2001, 1284. (b) Bach, T.; Bartels, M. Tetrahedron Lett. 2002, 43, 9125.
78. (a) Kelly, T. R.; Szabados, A.; Lee, Y.-J. J. Org. Chem. 1997, 62, 428.
79. (b) Suzuki, H.; Tsutsui, H.; Kano, A.; Katoh, S.; Morita, T.; Matsuda, M.; Iibuchi, N.; Ogawa, M. Heterocycles 1997, 45, 1657.
80. (c) Tanaka, H.; Kawakami, Y.; Kuroboshi, M.; Toru, S. Heterocycles 2001, 54, 825.
81. Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
82. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon Press: Oxford, 2002, 111-135.
83. Al-Ekabi, H.; de Mayo, P. J. Phys. Chem. 1985, 89, 5815.
84. Levacher, V.; Moberg, C. J. Org. Chem. 1995, 60, 1755.
85. Mabic, S.; Lepoittevin, J.-P. Tetrahedron Lett. 1995, 36, 1705.
86. Himmelreich, U.; Ripperger, H.; Anh, N. H.; Anh, U.; Sung, T. V. Magn. Res. Chem. 1995, 33, 280.