A general approach to indoles: Practical applications for the synthesis of highly functionalized pharmacophores

Chimia

Volumn 60, Issue 9, 2006, Pages 543-553

  Kuethe, Jeffrey T ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Dihydrobenzofuran; Indole; Nitrostyrene; Reductive cyclization

Indexed keywords

EID: 33749832654     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/chimia.2006.543     Document Type: Article

References (122)

1. a) R.J. Sundberg, 'The Chemistry of Indoles', Academic Press: New York, 1970;
2. b) R.J. Sundberg, 'Pyrroles and Their Benzo-derivatives: Synthesis and Applications', in 'Comprehensive Hetereocyclic Chemistry', Eds. A.R. Katritzky, C.W. Rees, Pergamon: Oxford, U.K., 1984, Vol. 4, pp 313-376;
3. c) R.J. Sundberg, in 'Best Synthetic Methods, Indoles', Academic Press: New York, 1996, pp 7-11;
4. d) J.A. Joule, 'Indole and its Derivatives', in 'Science of Synthesis: Houben-Weyl Methods of Molecular Transformation', Ed. E.J. Thomas, George Thieme Verlag: Stuttgart, Germany, 2000, Category 2, Vol. 10, Chapter 10.13;
5. e) R.K. Brown, in 'Indoles', Ed. W.J. Houlihan, Wiley-Interscience: New York, 1972;
6. f) R.J. Sundberg, in 'Comprehensive Heterocyclic Chemistry II', Eds. A.R. Katritzky, C.W. Rees, E.F.V. Scriven, C.W. Bird, Pergamon Press: Oxford, 1996, Vol. 2, p 119;
7. g) G.W. Gribble, in 'Comprehensive Heterocyclic Chemistry II', Eds. A.R. Katritzky, C.W. Rees, E.F.V. Scriven, C.W. Bird, Pergamon Press: Oxford, 1996, Vol. 2, p 207;
8. h) 'Indoles', Ed. R.J. Sundberg, Acedemic Press: London, 1996.
9. a) B.E. Evans, K.E. Rittle, M.G. Bock, R.M. DiPardo, R.M. Fridinger, W. L. Whitter, G.F. Lundell, D.F. Verber, P.S. Anderson, R.S.L. Chang, V.J. Lotti, D.H. Cerino, T.B. Chen, P.J. Kling, K.A. Kinkel, J.P. Springer, J. Hirshfield, J. Med. Chem. 1988, 31, 2235;
10. b) D.A. Horton, G.T. Bourne, M.L. Smythe, Chem. Rev. 2003, 103, 893 and references therein.
11. G.R. Humphrey, J.T. Kuethe, Chem. Rev. 2006, 106, 2875.
12. For other reviews on the synthesis of indoles, see: a) G.W. Gribble, J. Chem. Soc., Perkin Trans. 1 2000, 1045;
13. b) U. Pindur, R. Adam, J. Heterocycl. Chem. 1988, 25, 1;
14. T.L. Gilchrist, J. Chem. Soc., Perkin Trans. 1 2001, 2491.
15. a) P. Carmeliet, R.K. Jain, Nature 2000, 407, 249;
16. b) J. Folkman, Nature Med. 1995, 1, 27;
17. c) J. Folkman, N. Engl. J. Med. 1995, 333, 1757;
18. c) P. Traxler, Expert Opin. Ther. Targets 2003, 7, 215 and references therein.
19. a) D. De-Feo-Jones, D.C. Helmbrook, R.E. Jones, U.S. Patent Appl. US2002/0041880 A1, 2000;
20. b) M.E. Fraley, K.L. Arrington, M.T. Bilodeau, G.A. Hartman, W.F. Hoffman, Y. Kim, R.W. Hungate, U.S. Patent, 6306874 B1, 2001;
21. c) Merck & Co., Inc. World Intellectual Property Organization Patent WO 087651, 2004.
22. M.E. Fraley, W.F. Hoffman, K.L. Arrington, R.W. Hungate, G.D. Hartman, R.C. McFall, K.E. Coll, K. Rickert, K.A. Thomas, G.B. McGraughey, Curr. Med. Chem. 2004, 11, 709.
23. a) C.N. Johnson, G. Stemp, N. Anand, S.C. Stephen, T. Gallagher, Synlett 1998, 1025;
24. b) B. Danieli, G. Lesma, M. Martinelli, D. Passarell, I. Perettlo, A. Silvani, Tetrahedron 1998, 54, 14081;
25. c) T.D. Krizan, J.C. Martin, J. Am. Chem. Soc. 1983, 105, 6155;
26. d) S. Caron, J.M. Hawkins, J. Org. Chem. 1998, 63, 2054;
27. e) T. Hiyama, in 'Metal-Catalyzed Cross-Coupling Reactions' Eds. F. Diederich, P.J. Stang, Wiley-VCH, Weinheim, Germany, 1988; Chap. 10;
28. f) K. Tamao, K. Kobayashi, Y. Ito, Tetrahedron Lett. 1989, 30, 6051;
29. g) M. Mowery, P. DeShong, J. Org. Chem. 1999, 64, 1648;
30. h) M.H. Lee, S.P. Nolan, Org. Lett. 2000, 2, 2053;
31. i) S.E. Denmark, D. Wehrli, Org. Lett. 2000, 2, 565;
32. j) S.E. Denmark, L. Neuville, Org. Lett. 2000, 2, 3221;
33. k) S.E. Denmark, W. Pan, Org. Lett. 2001, 3, 61;
34. l) S.E. Denmark, J.D. Baird, Org. Lett. 2004, 6, 3649.
35. E. Vazquez, I.W. Davies, J.F. Payack, J. Org. Chem. 2002, 67, 7551.
36. J.F. Payack, E. Vazquez, L. Matty, M. H. Kress, J. McNamara, J. Org. Chem. 2005, 70, 175.
37. J.T. Kuethe, A. Wong, C. Qu, J. Smitrovich, I. W. Davies, D.L. Hughes, J. Org. Chem. 2005, 70, 2555.
38. J.L. Rutherford, M.P. Rainka, S.L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168.
39. T. Iwama, V.B. Birman, S.A. Kozmin, V.H. Rawal, Org. Lett. 1999, 1, 673.
40. a) T.V. RajanBabu, G.S. Reedy, T. Fukunaga, J. Am. Chem. Soc. 1985, 107, 5473;
41. b) T.V. RajanBabu, B.L. Chenard, M.A. Petti, J. Org. Chem. 1986, 51, 1704.
42. M.G. Banwell, B.D. Kelly, O.J. Kokas, D.W. Lupton, Org. Lett. 2003, 5, 2497.
43. A. Ricci, M. Fochi, Angew. Chem. Int. Ed. 2003, 42, 1444 and references therein.
44. R.M. Jacob, German Patent DE 828695, 1950.
45. G. Bartoli, M. Bosco, D. Caretti, R. Dalpozzo, R.E. Todesco, J. Org. Chem. 1986, 51, 3694.
46. G. Bartoli, M. Bosco, D. Caretti, R. Dalpozzo, R.E. Todesco, J. Org. Chem. 1987, 52, 4381.
47. a) J.D. Albright, L. Goldman, J. Am. Chem. Soc. 1965, 87, 4214;
48. b) J.D. Albright, L. Goldman, J. Am. Chem. Soc. 1967, 89, 2416.
49. A. Wong, J.T. Kuethe, I.W. Davies, D.L. Hughes, J. Org. Chem. 2004, 69, 7761.
50. a) R.J. Sundberg, J. Org. Chem. 1965, 30, 3604;
51. b) R.J. Sundberg, T. Yamazaki, J. Org. Chem. 1967, 32, 290;
52. c) P.M. Fresneda, P. Molina, S. Delgado, Tetrahedron 2001, 57, 6197.
53. For leading references, see: a) S.W. Dantale, B.C.G. Söderberg, Tetrahedron 2003, 59, 5507;
54. b) T.L. Scott, B.C.G. Söderberg, Tetrahedron Lett. 2002, 43, 1621;
55. c) B.C.G. Söderberg, J.A. Shriver, J. Org. Chem. 1997, 62, 5838;
56. d) B.C. Söderberg, S.R. Rector, S.N. O'Neil, Tetrahedron Lett. 1999, 40, 3657.
57. a) J.I.G. Cadogan, M. Cameron-Wood, Proc. Chem. Soc. 1962, 361;
58. b) J.I.G. Cadogan, R.K. Mackie, M.J. Todd, J. Chem. Soc., Chem. Commun. 1966, 491.
59. a) R.J. Sundberg, J. Org. Chem. 1965, 30, 3604;
60. b) R.J. Sundberg, T. Tamazaki, J. Org. Chem. 1967, 32, 290.
61. I.W. Davies, J.H. Smitrovich, R. Sidler, C. Qu, V. Gresham, C. Bazaral, Tetrahedron 2005, 61, 6425.
62. For reviews, see: a) B.C.G. Söderberg, Curr. Org. Chem. 2000, 4, 727;
63. b) P.G. Tsoungas, A.I. Diplas, Curr. Org. Chem. 2004, 8, 1579.
64. J.T. Kuethe, A. Wong, I.W. Davies, Org. Lett. 2003, 5, 3975.
65. H. Horstmann, P. Andrews, R. Goennert, Eur. J. Med. Chem. 1980, 15, 399.
66. For leading references, see: a) J. Bergman, T. Janosik, N. Wahlström, Adv. Heterocycl. Chem. 2001, 80, 1;
67. b) U. Pindur, Y.-S. Kim, Curr. Med. Chem. 1999, 6, 29;
68. c) J. Bergman, Stud. Nat. Prod. Chem., A 1988, 1, 3;
69. d) W. Steglich, Fortschr. Chem. Org. Naturst. 1987, 51, 216;
70. e) G.W. Gribble, S.J. Berthel, Stud. Nat. Prod. Chem. 1993, 12, 365;
71. f) M. Prudhomme, Curr. Pharm. Design 1997, 3, 265.
72. a) T. Tamaoki, H. Nomoto, I. Takahishi, Y. Kato, M. Morimoto, F. Tomita, Biochem. Biophy. Res. Commun. 1986, 135, 397;
73. b) S. Omura, Y. Sasaki, T. Iwai, H. Takashima, J. Antibiot. 1995, 48, 535.
74. M.J. Slater, S. Cockerill, R. Baxter, R.W. Bonser, K. Gohil, C. Gowrie, J.E. Robinson, E. Littler, N. Parry, R. Randall, W. Snowden, Bioorg. Med. Chem. 1999, 7, 1067.
75. J.T. Kuethe, A. Wong, I.W. Davies, Org. Lett. 2003, 5, 3721.
76. For the synthesis of substituted indolocarbazoles from 2,2′-biindoles, see: a) J.L. Wood, B.M. Stoltz, H.-J. Dietich, J. Am. Chem. Soc. 1995, 117, 10413;
77. b) J.L. Wood, B.M. Stoltz, H.-J. Dietrich, D.A. Pflum, D.T. Petsch, J. Am. Chem. Soc. 1997, 119, 9641.
78. T. Janosik, J. Bergman, Tetrahedron 1999, 55, 2371.
79. A. Akao, S. Hiraga, T. Iida, A. Kamatani, M. Kawasaki, T. Mase, T. Nemoto, N, Satake, S.A. Weissman, D.M. Tschaen, K. Rossen, D. Petrillo, R.A. Reamer, R.P. Volante, Tetrahedron 2001, 57, 8917.
80. T. Iversen, D.R. Bundle, Carbohydr. Res. 1982, 103, 29.
81. J.T. Kuethe, I.W. Davies, Tetrahedron Lett. 2004, 45, 4009.
82. G. Thoma, F. Nuninger, M. Schaefer, K.G. Akyel, R. Albert, C. Beerli, C. Bruns, E. Francotte, M. Luyten, D. MacKenzie, L. Oberer, M.B. Streiff, T. Wagner, H. Walter, G. Weckbecker, H.-G. Zerwes, J. Med. Chem. 2004, 47, 1939.
83. K. Kumar, D. Michalik, I.G. Castro, T. Tillack, A. Zapf, M. Arlt, T. Heinrich, H. Boettcher, M. Beller, Chem. Eur. J. 2004, 10, 746.
84. A. Palani, S. Dugar, J.W. Clader, W.J. Greenlee, V. Ruperto, R.A. Duffy, J.E. Lachowicz, Bioorg. Med. Chem. Lett. 2004, 14, 1791.
85. A. Kakefuda, T. Watanabe, Y. Taguchi, N. Masuda, A. Tanaka, I. Yanagisawa, Chem. Pharm. Bull. 2003, 51, 390.
86. Y. Dai, Y. Guo, J. Guo, L.J. Pease, J. Li, P.A. Marcotte, K.B. Glaser, P. Tapang, D.H. Albert, P.L. Richardson, S.K. Davidsen, M.R. Michaelides, Bioorg. Med. Chem. Lett. 2003, 13, 3087.
87. B.J. Mavunkel, S. Chakravarty, J.J. Perumattam, G.R. Luedtke, X. Liang, D. Lim, Y.J. Xu, M. Laney, D.Y. Liu, G.F. Schreiner, J.A. Lewicki, S. Dugar, Bioorg. Med. Chem. Lett. 2003, 13, 3087.
88. A.-M. Chollet, T.L. Diguarher, N. Kucharczyk, A. Loynel, M. Bertrand, G. Tucker, N. Guilbaud, M. Burbridge, P. Pastoureau, A. Fradin, M. Sabatini, J.-L. Fauchère, P. Casara, Bioorg. Med. Chem. Lett. 2002, 10, 531.
89. S.S.C. Koch, L.H. Thoresen, J.G. Tikhe, K.A. Maegley, R.J. Almassy, J. Li, X.-H. Yu, S.E. Zook, R.A. Kumpf, C. Zhang, T.J. Boritzki, R.N. Mansour, K.E. Zhang, A. Ekker, C.R. Calabrese, N.J. Curtin, S. Kyle, S.E. Thomas, L.-Z. Wang, A.H. Calvert, B.T. Golding, R.J. Griffin, D.R. Newell, S.E. Webber, Z. Hostomsky, J. Med. Chem. 2002, 45, 4961.
90. For leading references, see: K. Kumar, A. Zapf, D. Michalik, A. Tillack, T. Heinrich, H. Böttcher, M. Arlt, M. Beller, Org. Lett. 2004, 6, 7 and references cited therein.
91. J.T. Kuethe, I.W. Davies, Tetrahedron 2006, 62, doi: 10.1016/j.tet.2006. 05.007.
92. For reviews on N-hydroxyindoles and their derivatives, see: a) M. Somei, Adv. Heterocycl. Chem. 2002, 82, 101;
93. b) M. Somei, Heterocycles 1999, 50, 1157;
94. c) R.M. Acheson, Adv. Heterocycl. Chem. 1990, 51, 105;
95. d) M. Somei, Yuki Gosei Kogaku Kyokaishi 1991, 49, 205;
96. e) R.M. Acheson, in 'New Trends in Heterocyclic Chemistry' Eds. R.B. Mitra, N.R. Ayyanger, Y.N. Gogte, R.M. Acheson, N. Cromwell, Elsevier Science Publishers: New York, 1979; p. 1.
97. a) M. Somei, T. Kawasaki, Heterocycles 1989, 29, 1251;
98. b) T. Kawasaki, A. Kodama, T. Nishida, K. Shimizu, M. Somei, Heterocycles 1991, 32, 221.
99. A. Wong, J.T. Kuethe, I.W. Davies, J. Org. Chem. 2003, 68, 9865.
100. See ref. [49] and references cited therein.
101. G.R. Srinivasa, K. Abiraj, D.C. Gowda, Tetrahedron Lett. 2003, 44, 5835.
102. P. Strazzolini, A.G. Giumanini, A. Runcio, M. Scuccato, J. Org. Chem. 1998, 63, 952.
103. For the isolation of 123, see: K. Monde, M. Takasugi, A. Shirata, Phytochemistry 1995, 59, 581.
104. For the use of 123 in natural product synthesis, see a) ref. [47];
105. b) M. Somei, H. Ohnishi, Y. Shoken, Chem. Pharm. Bull. 1986, 34, 677;
106. c) R.M. Acheson, P.G. Hunt, D.M. Littlewood, B.A. Murrer, H.E. Rosenburg, J. Chem. Soc., Perkin Trans. 1 1978, 1117.
107. a) B.J. Donnelly, M.X. Donnelly, A.M. O'Sullivan, J.P. Prendergast, Tetrahedron 1969, 25, 4409;
108. b) T. Hayashi, R.H. Thomson, Phytochemistry 1975,14, 1085;
109. c) M. Gregson, W.D. Ollis, B.T. Redman, I.O. Sutherland, H.H. Dietrichs, O.R. Gottlieb, Phytochemistry 1978, 17, 1395;
110. d) R.S. Ward, Nat. Prod. Rep. 1995, 12, 183;
111. e) R.S. Ward, Nat. Prod. Rep. 1997, 14, 43;
112. f) P.J.C. Benevides, P. Sartorelli, M.J. Kato, Phytochemistry 1999, 52, 339;
113. g) I.R. Nascimento, L.M.X. Lopes, Phytochemistry 1999, 52, 345;
114. h) M. Gordaliza, M. Castro, J.M. Corral, M. Lopez-Vazquez, A.S. Feliciano, G.T. Faircloth, Bioorg. Med. Chem. Lett. 1997, 7, 2781;
115. i) I.-L. Tsai, C.-F. Hsieh, C.-Y. Duh, Phytochemistry 1998, 48, 1371;
116. j) C.-H. Chen, C.-Y. Shaw, C.-C. Chen, T.-C. Tsai, J. Nat. Prod. 2002, 65, 740;
117. k) S. Apers, D. Paper, J. Bürgermeister, S. Baronikova, S. Van Dyck, G. Lemière, A. Vlietinck, L. Pieters, J. Nat. Prod. 2002, 65, 718;
118. l) P. Satorelli, P.J.C. Benevides, R.M. Ellensohn, M.V.A.F. Rocha, P.R.H. Moreno, M.J. Kato, Plant Sci. 2001, 161, 1083.
119. S. Ohkawa, K. Fukatsu, S. Miki, T. Hashimoto, J. Sakamoto, T. Doi, Y. Nagai, T. Aono, J. Med. Chem. 1997, 40, 559.
120. T. Aono, S. Ohkawa, T. Doi, EP Patent 483772, 1992.
121. J.T. Kuethe, A. Wong, M. Journet, I.W. Davies, J. Org. Chem. 2005, 70, 3727.
122. Unpublished results from the Author.