Recent advances in the synthesis and application of benzocyclobutenones and related compounds

Synthesis (Germany)

Volumn 45, Issue 5, 2013, Pages 563-580

  Flores Gaspar, Areli ^a   Martin, Ruben ^a  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

benzocyclobutenones; C C bond cleavage; cycloaddition; fused aromatic systems; o quinone dimethides; ring expansion

Indexed keywords

ANNULENES; AROMATIC SYSTEM; BENZOCYCLOBUTENONES; BENZODIAZEPINES; C-C BOND CLEAVAGES; CARBON-CARBON BOND CLEAVAGE; CYCLOADDITIONS; ELECTROPHILICITY; FIVE-MEMBERED RINGS; FUSED RING; HIGH REACTIVITY; INTRAMOLECULAR CYCLIZATIONS; METAL-CATALYZED CROSS-COUPLING REACTIONS; NAPHTHALENE DERIVATIVES; NATURAL PRODUCT SYNTHESIS; NATURAL PRODUCTS; ORGANIC SYNTHESIS; POLYCYCLIC COMPOUNDS; RELATED COMPOUNDS; RING EXPANSION; SIX-MEMBERED RINGS; STILLE CROSS-COUPLING; SYNTHETIC APPLICATION; SYNTHETIC INTERMEDIATES; SYNTHETIC METHODS; TETRAHYDRONAPHTHALENES;

AROMATIC COMPOUNDS; CYCLIZATION; CYCLOADDITION; KETONES; NAPHTHALENE;

SYNTHESIS (CHEMICAL);

ANNULENE DERIVATIVE; ANTHRAQUINONE DERIVATIVE; ANTIBIOTIC AGENT; AQUAYAMYCIN; AROMATIC COMPOUND; BENZOCYCLOBUTENONE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; CARBON; CARBONYL DERIVATIVE; CHROMIUM DERIVATIVE; DEACETYLRAVIDOMYCIN M; DEFUCOGILVOCARCIN M; HYDROGEN; ISOCHROMANONE DERIVATIVE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; METAL DERIVATIVE; MYCOPHENOLIC ACID; NANAOMYCIN D; NAPHTHALENE DERIVATIVE; NATURAL PRODUCT; ORGANIC COMPOUND; PALLADIUM; PHTHALIDE DERIVATIVE; POLYCYCLIC HYDROCARBON; QUINONE DIMETHIDE DERIVATIVE; SPIRONOLACTONE; TETRALIN DERIVATIVE; TRICARBONYLCHROMIUM DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALDOL REACTION; CATALYSIS; CHEMICAL REACTION; CHEMOSENSITIVITY; CROSS LINKING; CYCLIZATION; CYCLOADDITION; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHILICITY; HYDROGEN BOND; QUANTUM YIELD; REACTION ANALYSIS; REVIEW; STILLE REACTION; STRUCTURE ANALYSIS;

EID: 84874258232     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316850     Document Type: Review

References (107)

1. Small Ring Compounds in Organic Synthesis, In Topics in Current Chemistry; Vol. 6; de Meijere, A., Ed.; Springer: Berlin, 2000, 1-230.
2. Strained Organic Molecules; Greenberg, A.; Liebman, J. F., Eds.; Academic Press: New York, 1978.
3. Seiser, T.; Saget, T.; Tran, D. N.; Cramer, N. Angew. Chem. Int. Ed. 2011, 50, 7740.
4. Sadana, A. K.; Saini, R. K.; Billups, W. E. Chem. Rev. 2003, 103, 1539.
5. Mehta, G.; Kotha, S. Tetrahedron 2001, 625.
6. Bellus, D.; Ernst, B. Angew. Chem. Int. Ed. 1988, 27, 797.
7. Liebman, J. F.; Greenberg, A. Chem. Rev. 1976, 76, 311.
8. Thummel, R. P. Acc. Chem. Res. 1980, 13, 70.
9. Klundt, I. L. Chem. Rev. 1970, 70, 471.
10. Tadross, P. M.; Stolz, B. M. Chem. Rev. 2012, 112, 3550.
11. Chen, Y.; Larock, R. C. Arylation Reactions involving the formation of arynes, In Modern Arylation Methods; Ackermann, L., Ed.; Wiley- VCH: Weinheim, 2009.
12. Sanz, R. Org. Prep. Proced. Int. 2008, 40, 215.
13. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem. Int. Ed. 2003, 42, 502.
14. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701.
15. Reinecke, M. G. Tetrahedron 1982, 38, 427.
16. Stevens, R. V.; Bisacchi, G. S. J. Org. Chem. 1982, 47, 2393.
17. Maurin, P.; Ibrahim-Ouali, M.; Santelli, M. Eur. J. Org. Chem. 2002, 151.
18. Maurin, P.; Ibrahim-Ouali, M.; Santelli, M. Tetrahedron Lett. 2001, 42, 8147.
19. Mariet, N.; Ibrahim-Ouali, M.; Santelli, M. Tetrahedron Lett. 2002, 43, 5789.
20. Im, G. Y. J.; Bronner, S. M.; Goetz, A. E.; Paton, R. S.; Cheong, P. H. Y.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2010, 132, 17933.
21. Bronner, S. M.; Bahnck, K. B.; Garg, N. K. Org. Lett. 2009, 11, 1007.
22. Hosoya, T.; Kuriyama, Y.; Suzuki, K. Synlett 1995, 177.
23. Hamura, T.; Hosoya, T.; Yamaguchi, H.; Kuriyama, Y.; Tanabe, M.; Miyamoto, M.; Yasui, Y.; Matsumoto, T.; Suzuki, K. Helv. Chim. Acta 2002, 85, 3589.
24. Hosoya, T.; Hamura, T.; Kuriyama, Y.; Miyamoto, M.; Matosumoto, T.; Suzuki, K. Synlett 2000, 520.
25. Hamura, T.; Ibusuki, Y.; Sato, K.; Matsumoto, T.; Osamura, Y.; Suzuki, K. Org. Lett. 2003, 5, 3551.
26. Hamura, T.; Ibusuki, Y.; Uekusa, H.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 2006, 128, 3534.
27. Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 3377.
28. Bronner, S. M.; Mackey, J. L.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2012, 134, 13966.
29. Goetz, A. E.; Bronner, S. M.; Cisneros, J. D.; Melamed, J. M.; Paton, R. S.; Houk, K. N.; Garg, N. K. Angew. Chem. Int. Ed. 2012, 51, 2758.
30. Bronner, S. M.; Goetz, A. E.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 3832.
31. Aidhen, I. S.; Ahuja, J. R. Tetrahedron Lett. 1992, 33, 5431.
32. Metal-catalyzed Cross-coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
33. Martin, R.; Buchwald, S. L. Org. Lett. 2008, 10, 4561.
34. Vo, G. D.; Hartwig, J. F. Angew. Chem. Int. Ed. 2008, 47, 2127.
35. Martin, R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2007, 46, 7236.
36. Álvarez-Bercedo, P.; Flores-Gaspar, A.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2010, 132, 466.
37. Leung, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202.
38. Willis, M. C. Chem. Rev. 2010, 110, 725.
39. Li, C.; Wang, L.; Li, P.; Zhou, W. Chem. Eur. J. 2011, 17, 10208.
40. Tang, B.; Song, R.; Wu, C.; Liu, Y.; Zhou, M.; Wei, W.; Deng, G.; Yin, D.; Li, J.-H. J. Am. Chem. Soc. 2010, 132, 8900.
41. Baslé, O.; Bidange, J.; Shuai, Q.; Li, C.-J. Adv. Synth. Catal. 2010, 352, 1145.
42. Sangwon, K.; Byungman, K.; Chang, S. Angew. Chem. Int. Ed. 2005, 44, 455.
43. Satoh, T.; Itaya, T.; Miura, M.; Nomura, M. Chem. Lett. 1996, 823.
44. Martin, R.; Flores-Gaspar, A. Org. Synth. 2012, 89, 159.
45. Yeung, C. S.; Dong, M. V. Chem. Rev. 2011, 111, 1215.
46. Hartwig, J. F. Chem. Soc. Rev. 2011, 40, 1992.
47. McMurray, L.; O'Hara, F. O.; Gaunt, M. Chem. Soc. Rev. 2011, 40, 1885.
48. Lyons, T. W.; Sanford, M. Chem. Rev. 2010, 110, 1147.
49. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem. Int. Ed. 2009, 48, 9792.
50. Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J.-Q. Angew. Chem. Int. Ed. 2009, 48, 5094.
51. Flores-Gaspar, A.; Martin, R. Adv. Synth. Catal. 2011, 353, 1222.
52. Kersharwani, T.; Verma, A. K.; Emrich, D.; Ward, J. A.; Larock, R. C. Org. Lett. 2009, 11, 2591.
53. Novák, P.; Martin, R. Curr. Org. Chem. 2011, 15, 3233.
54. Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082.
55. Johansson, C. C. C.; Colacot, T. J. Angew. Chem. Int. Ed. 2010, 49, 676.
56. Butoloso, A. C. Synlett 2009, 20, 320.
57. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234.
58. Flores-Gaspar, A.; Gutiérrez-Bonet, A.; Martin, R. Org. Lett. 2012, 14, 5234.
59. Dröge, T.; Glorius, F. Angew. Chem. Int. Ed. 2010, 49, 6940.
60. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem. Int. Ed. 2007, 46, 2768.
61. Christmann, U.; Vilar, R. Angew. Chem. Int. Ed. 2005, 44, 366.
62. Edwards, J. P.; Krysan, D. J.; Liebeskind, L. S. J. Org. Chem. 1993, 58, 3942.
63. Bradley, J. C.; Durst, T. J. Org. Chem. 1991, 56, 5459.
64. Yoshioka, M.; Arai, M.; Nishizawa, K.; Hasegawa, T. J. Chem. Soc., Chem. Commun. 1990, 374.
65. Yoshioka, M.; Momose, S.; Nishizawa, K.; Hasegawa, T. J. Chem. Soc., Perkin Trans. 1 1992, 499.
66. Yoshioka, M.; Nishizawa, K.; Arai, M.; Hasegawa, T. J. Chem. Soc., Perkin Trans. 1 1991, 541.
67. Hickman, D. N.; Hodgetts, K. J.; Mackman, P. S.; Wallace, T. W.; Wardleworth, J. M. Tetrahedron 1996, 52, 2235.
68. Lee, J.; Hong, J. J. Org. Chem. 2004, 69, 6433.
69. Feldman, K. S.; Ngernmeesri, P. Org. Lett. 2011, 13, 5704.
70. Graening, T.; Schmalz, H. G. Angew. Chem. Int. Ed. 2004, 43, 3230.
71. Choy, W.; Yang, H. J. Org. Chem. 1988, 53, 5796.
72. Garcia-Garcia, P.; Novillo, C.; Fernandez-Rodriguez, M. A.; Aguilar, E. Chem. Eur. J. 2011, 17, 564.
73. Hamura, T.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 280.
74. Bungard, C. J.; Morris, J. C. J. Org. Chem. 2002, 67, 2361.
75. Hamura, T.; Suzuki, T.; Matsumoto, T.; Suzuki, K. Angew. Chem. Int. Ed. 2006, 45, 6294.
76. Fitzgerald, J. J.; Michael, F. E.; Olofson, R. A. Tetrahedron Lett. 1994, 35, 9191.
77. Liebeskind, L. S.; Iyer, S.; Jewell, A. F. J. Org. Chem. 1986, 51, 3067.
78. Jackson, D. K.; Narasimhan, L.; Swenton, J. S. J. Am. Chem. Soc. 1979, 101, 3989.
79. Swenton, J. S.; Anderson, D. K.; Jackson, D. K.; Narasimhan, L. J. Org. Chem. 1981, 46, 4825.
80. Tiedemann, R.; Heileman, M. J.; Moore, H. W. J. Org. Chem. 1999, 64, 2170.
81. Suzuki, T.; Hamura, T.; Suzuki, K. Angew. Chem. Int. Ed. 2008, 47, 2248.
82. Matsuya, Y.; Ohsawa, N.; Nemoto, H. J. Am. Chem. Soc. 2006, 128, 13072.
83. Charlton, J. L.; Bogucki, D.; Guo, P. Can. J. Chem. 1995, 73, 1463.
84. Charlton, J. L.; Maddafort, S.; Koh, K.; Boulet, S.; Saunders, M. H. Tetrahedron: Asymmetry 1993, 4, 465.
85. Charlton, J. L.; Koh, K. Synlett 1990, 333.
86. Coll, G.; Costa, A.; Deyá, P. M.; Flexas, F.; Rotger, C.; Saá, J. M. J. Org. Chem. 1992, 57, 6222.
87. Allen, J. G.; Hentemman, M. F.; Danishefsky, S. J. J. Am. Chem. Soc. 2000, 122, 571.
88. Hentemman, M. F.; Allen, J. G.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2000, 39, 1937.
89. Matsumoto, T.; Hamura, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1997, 38, 8985.
90. Kohser, S. C.; Dongol, K. G.; Butenschon, H. Heterocycles 2007, 74, 339.
91. Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908.
92. Nemoto, H.; Shiraki, M.; Fukumoto, K. J. Org. Chem. 1996, 61, 1347.
93. Stone, G. B.; Liebeskind, L. S. J. Org. Chem. 1990, 55, 4614.
94. Ziehe, H.; Wartchow, R.; Butenschön, H. Eur. J. Org. Chem. 1999, 823.
95. Hayashi, T.; Ohmori, K.; Suzuki, K. Chem. Lett. 2011, 40, 612.
96. Meyer, A.; Imming, P. J. Nat. Prod. 2011, 74, 2482.
97. Orhan, I.; Berrin, Ö.; Bilge, S. Top. Heterocycl. Chem. 2007, 11, 303.
98. Abou-Donia, A. H. A.; El-Masry, S.; Saleh, M. R. I.; Phillipson, J. D. Planta Med. 1980, 40, 295.
99. Yoganathan, K.; Rossant, C.; Huang, Y.; Butler, M. S.; Buss, A. D. J. Nat. Prod. 2003, 66, 1116.
100. Arnone, A.; Assante, G.; Nasini, G.; Strada, S.; Vercesi, A. J. Nat. Prod. 2002, 65, 48.
101. Covarrubias-Zuñiga, A.; Gonzalez-Lucas, A.; Domínguez, M. M. Tetrahedron 2003, 59, 1989.
102. Patterson, J. W. J. Org. Chem. 1995, 60, 4542.
103. Yudin, A. K. Catalyzed Carbon-Heteroatom Bond Formation; Wiley-VCH: Weinheim, 2011, 35.
104. Kobayashi, K.; Itoh, M.; Sasaki, A.; Suginome, H. Tetrahedron 1991, 47, 5437.
105. Kobayashi, K.; Itoh, M.; Suginome, H. Tetrahedron Lett. 1987, 28, 3369.
106. Hosoya, T.; Kuriyama, Y.; Suzuki, K. Synlett 1995, 635.
107. Cho, H.; Iwama, Y.; Sugimoto, K.; Mori, S.; Tokuyama, H. J. Org. Chem. 2010, 75, 627.