Mucochloric and mucobromic acids: Inexpensive, highly functionalised starting materials for the selective synthesis of variously substituted 2(5H)-furanone derivatives, sulfur- or nitrogen-containing heterocytes and stereodefined acyclic unsaturated dihalogenated compounds

Current Organic Chemistry

Volumn 8, Issue 12, 2004, Pages 1089-1103

  Bellina, Fabio ^a   Rossi, Renzo ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; NITROGEN; UNSATURATED COMPOUNDS;

2(5H)-FURANONE; FUNCTIONALIZED; FURANONE DERIVATIVES; HETEROCYCLES; MUCOBROMIC ACIDS; MUCOCHLORIC; NATURAL PRODUCTS; SELECTIVE SYNTHESIS; SYNTHETIC APPLICATION; SYNTHONS;

SULFUR;

3,4 DIBROMO 5 HYDROXY 2(5H) FURANONE; AGRICULTURAL CHEMICAL; ANALGESIC AGENT; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; COMBRETASTATIN A4; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; FURANONE DERIVATIVE; HETEROCYCLIC COMPOUND; MUCOCHLORIC ACID; NATURAL PRODUCT; NITROGEN DERIVATIVE; ORGANIC COMPOUND; ROFECOXIB; RUBROLIDE C; RUBROLIDE E; RUBROLIDE M; RUBROLIDE N; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

AGRICULTURE; ANTIINFLAMMATORY ACTIVITY; CANCER CELL CULTURE; CHEMICAL REACTION; COST; CYTOTOXICITY; DRUG ACTIVITY; DRUG POTENCY; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; HALOGENATION; HUMAN; MATERIALS; NONHUMAN; PRECURSOR; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 3242756603     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043370195     Document Type: Review

References (155)

1. Ortega, J. J.; Zubia, E.; Ocaña, J. M.; Naranjo, S.; Salvà, J. Tetrahedron, 2000, 56, 3963.
2. Surivet, J. P.; Vatele, J. M. Tetrahedron Lett., 1996, 37, 4373.
3. Rossi, R.; Bellina, F. Targets Heterocycl. Chem., 2002, 5, 169 and references therein.
4. Jung, J. H.; Pummangura, S.; Chaichantipyuth, S.; Patarapanich, C.; Fanwick, P. E.; Chang, C.-J.; McLaughlin, J. L. Tetrahedron, 1990, 46, 5043.
5. Dawidson, B. S.; Ireland, C. M. J. Nat. Prod., 1990, 53, 1036.
6. Miao, S.; Andersen, R. J. J. Org. Chem., 1991, 56, 6275.
7. Kuhnt, D.; Anke, T.; Besl, H.; Bross, M.; Herrmann, R.; Mocek, U.; Steffan, B.; Steglich, W. J. Antiobiot., 1990, 43, 1413.
8. Bohlmann, F.; Brindöpke, G.; Rastogi, R. C. Phytochemistry, 1982, 21, 695.
9. Larock, R. C.; Reifling, B. J. Org. Chem., 1978, 43, 131 and references therein.
10. Caine, D.; Stephen, F.; Uckachukawa, V. C. J. Org. Chem., 1983, 48, 740.
11. Desmond, R.; Dolling, U.; Marcune, B.; Tillyer, R.; Tschaen, D. World Patent WO96/08482, 21 March 1996.
12. Rao, Y. S. Chem. Rev., 1964, 64, 353.
13. Rao, Y. S. Chem. Rev., 1976, 76, 625.
14. Janini, T. E.; Sampson, P. J. Org. Chem., 1997, 62, 5069.
15. Grigg, R.; Kennewell, P.; Savic, V. Tetrahedron, 1994, 50, 5849.
16. Forgione, P.; Wilson, P. D.; Fallis, A. A. Tetrahedron Lett., 2000, 41, 17.
17. Mahon, R.; Richecoeur, A. M. E.; Sweeney, J. B. J. Org. Chem., 1999, 64, 328 and references therein.
18. Pattenden, G. Progr. Chem. Nat. Prod., 1978, 35, 133.
19. Knight, D. W. Contemp. Org. Synth., 1994, 1, 287.
20. Negishi, E-i.; Kotora, M. Tetrahedron, 1997, 53, 6707.
21. Brückner, R. Chem. Commun., 2001, 141.
22. Brückner, R. Current Org. Chem. 2001, 5, 679.
23. Carter, N. B.; Nadany, A. E.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1, 2002, 2324.
24. Simonis, H. Ber., 1901, 34, 509.
25. Hachihama, Y.; Shono, T.; Ikeda, S. J. Org. Chem., 1964, 29, 1371.
26. Dury, K. Angew. Chem., 1965, 77, 282.
27. Simonis, H. Ber, 1899, 32, 2085.
28. Taylor, G. A. Org. Synth. Coll., Vol, 4, 1963, 844.
29. Jackson, O. R.; Hill, H. B., Am. Chem. J., 1881, 3, 4.
30. Allen, C. F. H.; Spangler, F. W. Org. Synth. Coll., Vol 3, 1955, 621 and references therein.
31. Limpricht, H. Ann., 1873, 165, 283.
32. Buu-Hoï, N. P.; Dufour, M.; Jacquignon, P. Bull. Soc. Chim. Fr., 1971, 2999.
33. Wasserman, H. H.; Precopio, F. M. J. Am. Chem. Soc., 1952, 74, 326.
34. Mowry, D. T. J. Am. Chem. Soc., 1950, 72, 2535.
35. Moore, R. D.; Katon, J. E. Appl. Spectrosc., 1978, 32, 145.
36. Valente, E. J.; Fuller, J. F.; Ball, J. D. Acta Crystallogr., Sect. B Struct. Sci., 1998, B54, 162.
37. Kronberg, L.; Franzén, R. Environ. Sci. Technol., 1993, 27, 1811.
38. Tikkanen, L.; Kronberg, L. Mutat. Res., 1990, 240, 109.
39. Jansson, K.; Hyttinen, J. W.; Nittykoski, M.; Maki-Paakkanen, J. Environ. Mol. Mutag., 1995, 25, 284.
40. Lalonde, R. T.; Perakyla, H.; Cook, G. P.; Dence, C. W. Environ. Toxicol. Chem., 1990, 9, 687.
41. Lattmann, E.; Kinchington, D.; Singh, H.; Merinop, I.; Begum, A.; Ayuko, W. O.; Tisdale, M. J. Pharm. Pharmacol. Lett., 2001, 1, 5.
42. Shoppee, C. W. J. Chem. Soc., Perkin Trans. 1, 1985, 45.
43. Doerr, I. L.; Willette, R. E. J. Org. Chem., 1973, 38, 3878.
44. Lattmann, E.; Billington, D. C.; Langley, C. A. Drug Des. Discov., 1999, 16, 237.
45. Fishbein, P. L.; Moore, H. W. Synth. Commun., 1989, 19, 3283.
46. Chen, Q. H.; Huang, B. Chinese Chem Lett., 1993, 4, 675.
47. Fenske, D.; Merzweiler, K. Z. Naturforsch, B, 1989, 44, 879.
48. Ayuko, W. O.; Lattmann, E. PCT Int. Appl., WO 99/52888, 8 April 1999;
49. Ayuko, W. O.; Lattmann, E. Chem. Abstr. 1999, 131, 295577.
50. Krutisikova, A.; Korenova, A.; Kovac, J.; Konecny, V. Chem. Pap. - Chem. Zvesti, 1986, 40, 659.
51. Polezhaeva, N. A.; Sakhibullina, V. G.; El'shina, E. V.; Kostyunina, T. G.; Arbuzov, B. A. Zh. Obhsch. Klim., 1993, 63, 2422.
52. Kokosinski, J.; Gumulka, W. Organika, 1977, 37; Chem. Abstr. 1978, 89, 108874.
53. Krutisikova, A.; Konecny, V.; Kovac, J. Czech. Patent, Pat. Appl. CS84-8714, 1988;
54. Krutisikova, A.; Konecny, V.; Kovac, J. Chem. Abstr., 1988, 111, P 053601g.
55. Kokosinski, J. Organika, 1979, 24; Chem. Abstr. 1981, 94, 65402.
56. Dambeniece, I.; Karklina, A.; Gudriniece, E.; Petrova, M. V.; Ermakova, L. G. Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1989, 570;
57. Dambeniece, I.; Karklina, A.; Gudriniece, E.; Petrova, M. V.; Ermakova, L. G. Chem. Abstr. 1990, 112, 198002.
58. Jaehnisch., K.; Seeboth, H.; Pinon, D. Z. Chem., 1984, 24, 94.
59. Rees, C. W.; Sabet, C. R. J. Chem. Soc., 1965, 687.
60. Semonsky, M.; Hartl, J.; Krapelka, J.; Beran, M.; Kakac, B.; Vesela, H.; Rejholec, V. Collect. Czech. Chem. Commun., 1975, 40, 2869.
61. Garcia, G.; Ravina, E.; Santana, L.; Orallo, F.; Calleja, J. M. Anal. Real Acad. Farm., 1985, 51, 23.
62. Canevet, J. C.; Chiron, R. Ann. Pharm. 1982, 40, 481.
63. Semonsky, M.; Rockova, E.; Cerny, A.; Kakac, B.; Macek, K. Collect. Czech. Chem. Commun., 1962, 27, 1941.
64. Estevez, I.; Raviña, E.; Sotelo, E. J. Heterocyclic Chem., 1998, 35, 1421.
65. Heubach, G. Liebigs Ann. Chem., 1982, 1017.
66. Paulins, J.; Karklina, A.; Gudriniece, E. Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1979, 113;
67. Paulins, J.; Karklina, A.; Gudriniece, E. Chem. Abstr. 1979, 90, 186693.
68. Simonis, H.; Marben, E.; Mermod, E. Ber., 1905, 38, 3983.
69. Vinigradova, E. J.; Shemyakin, M. M. Zh. Obshch. Khim., 1946, 16, 709.
70. Zhang, J.; Blazecka, P. G.; Berven, H.; Delmont, D. Tetrahedron Lett., 2003, 44, 5579.
71. Ducher, S.; Michet, A. Bull. Soc. Chim. Fr., 1976, 1923.
72. Sulikowski, G. A.; Agnelli, F.; Corbett, R. M. J. Org. Chem., 2000, 65, 337.
73. Napolitano, A.; Bruno, I.; Gomez-Paloma, L.; Riccio, R. Giornate di Chimica delle Sostanze Naturali, Atti del VI Convegno Nazionale, Vietri sul Mare (SA), Italy, September 29-October 1, 2003, P66.
74. Ngwe, H.; Nakayama, E.; Higashi, T.; Kinoshita, H.; Inomata, K. Chem. Lett. 1995, 713.
75. Beska, E.; Rapos, P. J. Chem. Soc., Perkin Trans. 1, 1976, 2470.
76. Zhang, J.; Blazecka, P. G.; Belmont, D.; Davidson, J. G. Org. Lett., 2002, 4, 4559.
77. Cherkasov, R. A.; Polezhaeva, N. A.; Galkin, V. I. Ukr. Khim. Zh., 1999, 65, 21.
78. Polezhaeva, N. A.; Loginova, I. V.; Ovechkina, E. V.; Galkin, V. I.; Sakhibullina, V. G.; Cherkasov, R. A. Zh. Obshch. Khim., 1997, 67, 1076.
79. Polezhaeva, N. A.; Loginova, I. V.; Ovechkina, E. V.; Galkin, V. I.; Sakhibullina, V. G.; Cherkasov, R. A. Zh. Obshch. Khim., 1996, 66, 927.
80. Polezhaeva, N. A.; Loginova, I. V.; Ovechkina, E. V.; Galkin, V. I.; Sakhibullina, V. G.; Cherkasov, R. A.; Gubaidullin A. T.; Litvinov, I. A.; Naumov, V. A. Zh. Obshch. Khim., 2000, 70, 754.
81. Polezhaeva, N. A.; Volodina, Y. M.; Kalinina, I. V.; Sakhibullina, V. G.; Chmutova, G. A.; Galkin, V. I.; Cherkasov, R. A. Zh. Obshch. Khim., 2002, 72, 1283.
82. Ratts, K. W.; Phillips, W. G. J. Org. Chem., 1974, 39, 3300.
83. Arbuzov, B. A.; Polezhaeva, N. A.; El'shina, E. V. Zh. Obshch. Khim., 1988, 58, 1213.
84. Al-Hakim, A. H.; Haines, A. H. Tetrahedron Lett., 1982, 23, 5295.
85. Krutisikova, A.; Dandarova, M.; Konecny, V. Collect. Czech. Chem. Commun., 1990, 55, 2707.
86. Konecny, V.; Kovac, S. Chem. Pap.-Chem. Zvesti, 1987, 41, 107.
87. Konecny, V.; Kovac, S. Chem. Pap.-Chem. Zvesti, 1983, 37, 395.
88. Avota, L.; Egerts, V.; Tikhvinskaya, T. I.; Hillers, S. Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1976, 272;
89. Avota, L.; Egerts, V.; Tikhvinskaya, T. I.; Hillers, S. Chem. Abstr. 1976, 85, 123844.
90. Mowry, D. J. Am. Chem. Soc., 1953, 75, 1909.
91. Cheng, Z.; Gu, B. Nongayo, 2001, 40, 9.
92. Hartke, K.; Rauschen, F. J. Prakt. Chem., 1997, 15.
93. Jänisch, K.; Duczee, W. J. Prakt. Chem., 1990, 117.
94. Ngwe, H.; Nakayama, E.; Higashi, T.; Kinoshita, H.; Inomata, K. Chem. Lett., 1995, 713.
95. Zhang, J.; Blazecka, P. G.; Davidson, J. G. Org. Lett., 2003, 5, 553.
96. Homer, F.; Gregory, H.; Wiggins, L. F. J. Chem. Soc., 1946, 2191.
97. Schönbecke, R.; Kloimstein, K. Monatsh. Chem., 1968, 99, 15.
98. Chen, S.-F.; Panzica, R. P. J. Org. Chem., 1981, 46, 2473.
99. Makino, K.; Sakata, G. Heterocycles, 1985, 23, 2603.
100. Konecny, V.; Kovac, S.; Varkonda, S. Chem. Zvesti, 1984, 38, 239.
101. Sohler, E.; Hutar, E.; Rapos, P.; Truchlik, S.; Seidler, L.; Vanek, J. Czech. CS 197.194, 15 Aug 1983;
102. Sohler, E.; Hutar, E.; Rapos, P.; Truchlik, S.; Seidler, L.; Vanek, J. Chem. Abstr. 1984, 100, 5196.
103. Sohler, E.; Holcik, J.; Kacani, S.; Jancina, O.; Poor, R.; Lacko, J.; Zervan, I. Czech. CS 246.886, 15 Jan 1988;
104. Sohler, E.; Holcik, J.; Kacani, S.; Jancina, O.; Poor, R.; Lacko, J.; Zervan, I. Chem. Abstr. 1989, 110, 154308.
105. Kawazoe, T. Jpn. Kokai Tokkyo Koho, 06/001774, 11 Jan 1994;
106. Kawazoe, T. Chem. Abstr., 1994, 120, P 270437e.
107. Santagati, N. A.; Duro, F.; Caruso, A.; Trombadore, S.; Amico-Roxas, M. Farmaco, 1985, 40, 921.
108. Krutisikova, A.; Dandarova, M.; Konecny, V. Collect. Czech. Chem. Commun., 1990, 55, 2707.
109. Suzuki, H.; Kawamura, Y.; Ogura, T. Eur. Pat., Pat. Appl. EP 169375, 29 Jan 1986;
110. Suzuki, H.; Kawamura, Y.; Ogura, T. Chem. Abstr., 1986, 105, P 42829u.
111. Kawazoe, T. Jpn. Kokai Tokkyo Koho, 05/24942, 09 Nov 1993;
112. Kawazoe, T. Chem. Abstr., 1994, 120, P 77891v.
113. Takaya, M.; Sato, M.; Terashima, K.; Tanizawa, H. J. Med. Chem., 1979, 22, 53.
114. Okafor, C. O.; Castle, R. N. J. Heterocyclic Chem., 1983, 20, 199.
115. Dambeniece, I.; Karklina, A.; Petrova, M. V.; Gudriniece, E. Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1989, 563;
116. Dambeniece, I.; Karklina, A.; Petrova, M. V.; Gudriniece, E. Chem. Abstr. 1990, 112, 216572.
117. Reicheneder, F.; Dury, K. French Patent 1,352,099, 1964;
118. Reicheneder, F.; Dury, K. Chem. Abstr., 1964, 60, 13256.
119. Gallemaers, J-P.; Cristophe, D.; Promel, R. Tetrahedron Lett., 1976, 693.
120. Budesinskiy, Z.; Vavrina, J.; Langsdl, L.; Holubek, J. Collect. Czech. Chem. Commun., 1980, 45, 539.
121. Mäki, J.; Sjöholm, R.; Kronberg, L. J. Chem. Soc., Perkin Trans. 1, 1999, 2923.
122. Neunhoeffer, H.; Degen, H-J. Chem. Ber., 1975, 108, 3509.
123. Polezhaeva, N. A.; Volodina, Y. M.; Sakhibullina, V. G.; Loginova, I. V.; Galkin, V. I.; Cherkasov, R. A. Zh. Obshch. Khim., 2000, 70, 851.
124. Hill, H. B.; Cornelison, R. W. J. Am. Chem. Soc., 1894, 16, 277.
125. Bellina, F.; Anselmi, C.; Martina, F.; Rossi, R. Eur. J. Org. Chem., 2003, 2290.
126. Rossi, R.; Bellina, F.; Raugei, E. Synlett, 2000, 1749.
127. Bellina, F.; Anselmi, C.; Viel, S.; Mannina, L.; Rossi, R. Tetrahedron, 2001, 57, 9997.
128. Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett., 1998, 39, 7799.
129. Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron: Asymmetry, 1999, 10, 1163.
130. Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett., 1998, 39, 3017.
131. Rossi, R.; Bellina, F.; Biagetti, M. Synth. Commun., 1999, 29, 3415.
132. Rossi, R.; Bellina, F.; Catanese, A.; Mannina, L.; Valensin, D. Tetrahedron, 2000, 56, 479.
133. Bellina, F.; Ciucci, D.; Vergamini, D.; Rossi, R. Tetrahedron, 2000, 56, 2533.
134. Rossi, R.; Bellina, F.; Biagetti, M.; Catanese, A.; Mannina, L. Tetrahedron Lett., 2000, 41, 5281.
135. Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron, 2001, 57, 2857.
136. Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron Lett., 2001, 42, 2859.
137. Biagetti, M.; Bellina, F.; Carpita, A.; Viel, S.; Mannina, L.; Rossi, R. Eur. J. Org. Chem. 2002, 1063.
138. Biagetti, M.; Bellina, F.; Carpita, A.; Stabile, P. Rossi, R. Tetrahedron, 2002, 58, 5023.
139. Rossi, R.; Carpita, A.; Bellina, F.; Stabile, P.; Mannina, L. Tetrahedron, 2003, 59, 2067.
140. Biagetti, M.; Bellina, F.; Carpita, A.; Rossi, R. Tetrahedron Lett., 2003, 44, 607.
141. Bellina, F.; Anselmi, C.; Rossi, R. Tetrahedron Lett., 2001, 42, 3851.
142. Bellina, F.; Anselmi, C.; Rossi, R. Tetrahedron Lett., 2002, 43, 2023.
143. Bellina, F.; Rossi, R. Synthesis, 2002, 2729.
144. Bellina, F.; Falchi, E.; Rossi, R. Tetrahedron, 2003, 59, 2091.
145. Prasit, P.; Wang, Z.; Brideau, C.; Chan, C.-C.; Charleson, S.; Cromlish, W.; Ethier, D.; Evans, J. F.; Ford- Hutchison, A. W.; Gauthier, J. Y.; Gordon, R.; Guay, J.; Gresser, M.; Kargman, S.; Kennedy, B.; Leblanc, Y.; Legér, S.; Mancini, J.; O'Neill, G. P.; Ouellet, M.; Percival, M. D.; Perrier, H.; Riendeau, D.; Rodger, I.; Tagari, P.: Thérien, M.; Vickers, P.; Wong, E.; Xu, L.-J.; Young, R. N.; Zamboni, R. Bioorg. Med. Chem. Lett., 1999, 9, 1773.
146. Engel, G.; Teuber, M. In Mycotoxins-Production, Isolation. Separation and Purification; Betina, V., Ed.; Elsevier, Amsterdam, 1984, pp. 291-314.
147. Boukouvalas, J.; Lachance, N.; Ouelett, M.; Trudeau, M. Tetrahedron Lett., 1998, 39, 7665.
148. Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett., 1986, 27, 5541.
149. Evidente, A.; Randazzo, G.; Ballio, A. J. Nat. Prod., 1986, 49, 593.
150. Yang, X.; Shimizu, Y.; Steiner, J. R.; Clardy, J. Tetrahedron Lett., 1993, 34, 761.
151. Sonogashira, K. In Metal Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J.; Eds.; Wiley-VCH, Weinheim, 1998, Chapter 5, pp. 203-229.
152. Pettit, G. R.; Singh, S. B.; Boyd, M. R.; Hamel, E.; Pettit, R. K.; Schmidt, J. M.; Hogan, F. J. Med. Chem., 1995, 38, 1666.
153. Rahim, M. A.; Praven Rao, P. N.; Knaus, E. E. Bioorg. Med. Chem. Lett., 2002, 12, 2753.
154. Nam, N.-H.; Kim, Y.; You, Y.-J.; Hong, D.-H.; Kim, H.-M.; Ahn, B.-Z. Bioorg. Med. Chem. Lett., 2002, 12, 1955.
155. Bellina, F.; Rossi, R. 2003, unpublished results