Synthesis of xanthones: An overview

Current Medicinal Chemistry

Volumn 12, Issue 21, 2005, Pages 2447-2479

  Sousa, M E ^a   Pinto, M M M ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Benzophenone; Diphenyl ether; Heterocycle; Synthesis; Xanthene; Xanthenone; Xanthone

Indexed keywords

5,6 DIMETHYLXANTHONE 4 ACETIC ACID; ALPHA MANGOSTIN; ANTINEOPLASTIC AGENT; ATROVIRIDIN; BENZOPHENONE; BENZOXANTHONE DERIVATIVE; BIKAVERIN; CERVINOMYCIN A1; CERVINOMYCIN A2; DESOXYGAUDICHAUDIONE; DESOXYMORELLIN; DIHYDRO O METHYLSTERIGMATOCYSTIN; DNA TOPOISOMERASE INHIBITOR; ENZYME INHIBITOR; FORBESIONE; FURANOXANTHONE DERIVATIVE; GAMBOGIN; GARCINONE A; GENISTEIN; HYPOXYXYLERONE; ISOHYDROXYPSOROFEBRIN; ISOQUINOLINE DERIVATIVE; MORELLIN; NATURAL PRODUCT; O METHYLSTERIGMATOCYSTIN; PSOROSPERMIN; PYRANOXANTHONE DERIVATIVE; SECALONIC ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG; XANTHONE DERIVATIVE;

ACYLATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; REVIEW;

MOLECULAR STRUCTURE; XANTHONES;

EID: 26044481179     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986705774370736     Document Type: Review

References (212)

1. Hepworth, J.D. In Comprehensive Heterocyclic Chemistry; Boulton A.J.; McKillop, A., Eds.; Pergamon: Oxford, 1984; Vol. 3, pp. 835-840.
2. Peres, V.; Nagem, T.J. Phytochemistry, 1997, 44, 191.
3. Vieira, L.M.M.; Kijjoa; A. Natural Xanthones: Recent Developments. Curr. Med. Chem., 2005, 12, 2413.
4. Pinto, M.; Sousa, E.; Nascimento, M.S.J. Xanthone Derivatives: New Insigths in Biological Activities. Curr. Med. Chem., 2005, 12, 2517.
5. Michael, A. Ann. Chem. J., 1883, 5, 81.
6. Kostanecki. S. Ber., 1891, 24, 1898.
7. Wawzonek, S. In Heterocyclic Compounds; Elderfield, R. C., Ed.; Wiley, New York, 1950, 2, pp. 419-444.
8. Dean, F.M. In The Total Synthesis of Natural Products; Apsimon, J., Ed.; 1973, 1, pp. 534-562.
9. Afzal, M.; Al-Hassan, J.M. Heterocycles, 1980, 14, 1173.
10. Bringmann, G.; Ochse, M.; Schupp, O.; Tasler, S. In Progress in the Chemistry of Organic Natural Products; Springer: Wien, Germany, 2001, 82.
11. Grover, P.K.; Shah, G.D.; Shah, R.C. J. Chem. Soc., 1955, 3982.
12. Fonteneau, N.; Martin, P.; Mondon, M.; Ficheux, H.; Gesson, J.-P. Tetrahedron, 2001, 57, 9131.
13. Schwaebe, M.K.; Moran, T.J.; Whitten, J.P. Tetrahedron Lett., 2005, 46, 827.
14. Tisdale, E.J.; Slobodov, I.; Theodorakis, E. A. PNAS, 2004, 101, 12030.
15. Subba-Rao, G. S. R.; Raghavan, S. J. Indian Inst. Sci., 2001, 81, 393.
16. Janjie, N.; Schloeder, D.; Tramontano, A. J. Am. Chem. Soc., 1989, 11, 6374.
17. Coelho, P.J.; Carvalho, L.M.; Silva, J.C.; Oliveira-Campos, A.M.F.; Samat, A.; Guglielmetti, R. Helv. Chim. Acta, 2001, 84, 117.
18. Rampa, A.; Piazzi, L.; Belluti, F.; Gobbi, S.; Bisi, A.; Bartolini, M.; Andrisano, V.; Cavrini, V.; Cavalli, A.; Recanatini, M.; Valenti, P. J. Med. Chem., 2001, 44, 3810.
19. Gnerre, C.; Thull, U.; Gaillar, P.; Carrupt, P.A.; Testa, B.; Fernandes, E.; Silva, F.; Pinto, M.; Pinto, M.M.; Wolfender, J.L.; Hostettman, K.; Cruciani, G. Helv. Chim. Acta, 2001, 84, 552.
20. Ohishi, N.; Susuki, T.; Ogasawara, T.; Yagi, K. J. Molecular Catalysis B: Enzimatic, 2000, 10, 291.
21. Adams, S.R.; Campbell, R.E.; Gross, L.A.; Martin, B.R.; Walkup, G.K.; Yao, Y.; Llopis, J.; Tsien, R.Y. J. Am. Chem. Soc., 2002, 124, 6063.
22. Pedro, M.M.; Cerqueira, F.; Sousa, M.E.; Nascimento, M.S.J.; Pinto, M.M.M. Bioorg. Med. Chem., 2002, 10, 3725.
23. Ghirtis, K.; Pouli, N.; Marakos, P.; Skaltsounis, A.-L.; Leonce, S.; Caignard, D. H.; Atassi, G. Heterocycles, 2000, 53, 93.
24. Saraiva, L.; Fresco, P.; Pinto, E.; Sousa, E.; Pinto, M.; Gonçalves, J. Bioorg. Med. Chem., 2002, 10, 3219.
25. Madan, B.; Singh, I.; Kumar, A.; Prasad, A.; Raj, H.; Parmar, V.; Ghosh, B. Bioorg. Med. Chem., 2002, 10, 3431.
26. Pankajamani, K.S.; Seshadri, T.R. J. Sci. Industr. Res., 1954, 13B, 396.
27. Ruske, W. In Friedel-Crafts and Related Reactions; Olah, G. A., Ed.; Interscience Publishers, John Wiley & Sons: New York, 1964; pp. 383.
28. Quillinan, A.J.; Scheinmann, F. J. Chem. Soc. Perkin Trans. 1, 1973, 2, 1329.
29. Barton, D.H.R.; Scott, A.I. J. Chem. Soc., 1958, 1767.
30. Lewis, J.R. Proc. Chem. Soc., 1963, 373.
31. Moroz, A.A.; Shvartsberg, M.S. Russ. Chem. Rev., 1974, 43, 679.
32. Hassal, C.H.; Lewis, J.R. J. Chem. Soc., 1961, 2, 2312.
33. Kolokythas, G.; Kostakis, I.K.; Pouli, N.; Marakos, P.; Kletsas, D.; Pratsinis, H. Bioorg. Med. Chem., 2003, 11, 4591.
34. Bennet, O.F.; Bouchard, M.J.; Malloy, R.; Dervin, P.; Saluti, G. J. Org. Chem., 1972, 37, 1356.
35. Atwell, G.J.; Rewcastle, G.W.; Baguley, B.C.; Denny, W.A. J. Med. Chem., 1990, 33, 1375.
36. Finnegan, R.A.; Merkel, K.E. J. Org. Chem., 1972, 37, 2986.
37. Miller, J. A. J. Org. Chem., 1987, 52, 322.
38. Horne, S.; Rodrigo, R. J. Org. Chem., 1990, 55, 4520.
39. Horne, S.; Rodrigo, R. J. Chem. Soc. Chem. Commun., 1992, 164.
40. Nicolaou, K.C.; Bunnage, M.E.; Koide, K. J. Am. Chem. Soc., 1994, 116, 8402.
41. Lampe, P.F.; Hugues, C.K.; Biggers, C.K.; Smith, S.H.; Hu, H. J. Org. Chem., 1996, 61, 4572.
42. Couture, A.; Deniau, E.; Lebrun, S.; Grandclaudon, P. J. Chem. Soc. Perkin Trans. 1, 1999, 7, 789.
43. Elix, J.A.; Gaul, K.L.; Jiang, H. Aust. J. Chem., 1993, 46, 95.
44. Pfister, J. R. J. Heterocyclic. Chem. 1982, 19, 1255.
45. Tanase, Y. J. Pharm. Soc. Japan, 1941, 61, 341.
46. Pillai, R.K.M.; Naiksatam, P.; Johnson, F.; Rajagopalan, R.; Watts, P.C.; Cricchio, R.; Borras, S. J. Org. Chem., 1986, 51, 717.
47. Nishikawa, H.; Robinson, R. J. Chem. Soc., 1922, 121, 839.
48. Heymann, H. J. Amer. Chem. Soc., 1949, 71, 260.
49. Scott, A.I.; Pike, D.G; Ryon, J.J.; Guilford, H. Tetrahedron, 1971, 27, 3051.
50. Harris, T.M.; Hay, J.V. J. Am. Chem. Soc., 1977, 99, 1631.
51. Sandifer, R.M.; Bhattacharya, A.K.; Harris, T.M. J. Org. Chem., 1981, 46, 2260.
52. Muller, P.; Venakis, T.; Eugster, C.H. Helv. Chim. Acta, 1979, 62, 2350.
53. Vermes, B.; Seligmann O.; Wagner H. Helv. Chim. Acta, 1985, 68, 2359.
54. Moreau, S.; Varache-Lembege, M.; Larrouture, S.; Fall, D.; Neveu, A.; Deffieux, G.; Vercauteren, J.; Nuhrich, A. Eur. J. Med. Chem., 2002, 37, 237.
55. Olah, G.A.; Mathew, T.; Farnia, M.; Prakash, G.K.S. Synlett, 1999, 7, 1067.
56. Prakash, G.K.S.; Mathew, T.; Mandal, M.; Farnia, M.; Olah, G.A. Arkivoc, 2004, viii, 103.
57. Arimoto, H.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett., 1990, 31, 5619.
58. Yamamura, S.; Nishiyama, S. Bull. Chem. Soc. Jpn., 1997, 70, 2025.
59. Iikubo, K.; Ishikawa, Y.; Ando, N.; Umezawa, K.; Nishiyama, S. Tetrahedron Lett., 2002, 43, 291.
60. Patil, M.L.; Deshpande, V.H.; Ramlingam, S.; Borate, H.B. Tetrahedron, 2004, 60, 1869.
61. Patek, M.; Lebl, M.; Budesinsky, M. Tetrahedron Lett., 1992, 33, 4507.
62. Farrell, P.G.; Moskowitz, D.; Terrier, F. Synth. Comm., 1993, 23, 231.
63. Yamato, T.; Komine, M.; Nagano, Y. Org. Prep. Proced. Int., 1997, 29, 300.
64. Palomo, C.; Oiarbide, M.; Lopez, R.; Gomez-Bengoa, E. J. Chem. Soc. Chem. Commun., 1998, 2091.
65. Atwell, G.J.; Yang, S.; Denny, W.A. Eur. J. Med. Chem., 2002, 37, 825.
66. Familoni, O.B.; Ionica, I.; Bower, J.F.; Snieckus, V. Synlett., 1997, 1081.
67. Gales, L.; Sousa, M.E.; Pinto, M.M.M.; Kijjoa, A.; Damas, A. M. Acta Cryst., 2001, C57, 1319.
68. Yadav, J.S. Pure Appl. Chem., 1993, 65, 1349.
69. Gottlieb, O.R.; Mesquita, A.A.L.; Oliveira, G.G.; Melo, M.T. Phytochemistry, 1970, 9, 2537.
70. Davies, J.S.H.; Lamb; F.; Suschitzky, H. J. Chem. Soc., 1958, 1790.
71. Snieckus, V. Chem. Rev., 1990, 90, 879.
72. Fu, J.-M.; Zhao, B.P.; Sharp, M.J.; Snieckus, V. J. Org. Chem., 1991, 56, 1683.
73. Beaulieu, F.; Snieckus, V. J. Org. Chem., 1994, 59, 6508.
74. Brennan, N.K.; Donnelly, D.J.; Detty, M.R. J. Org. Chem., 2003, 68, 3344.
75. Jackson, W.T.; Boyd, R.J.; Froelich, L.L.; Gapinski, D.M.; Mallett, B.E.; Sawyer, J.S. J. Med. Chem., 1993, 36, 1726.
76. Bennetau, B.; Mortier, J.; Moyround, J.; Guesnet, J. J. Chem. Soc. Perkin Trans. 1, 1995, 1265.
77. Sousa, E.P.; Silva, A.M.S.; Pinto, M.M.M.; Pedro, M.M.; Cerqueira, F.A.M.; Nascimento, M.S.J. Helv. Chim. Acta, 2002, 85, 2862.
78. Cox, B.G.; Hurwood, T.V.; Prodi, L.; Montalti, M.; Bolletta, F.; Watt, C.I.F. J. Chem. Soc. Perkin Trans., 2, 1999, 2, 289.
79. Kristensen, J.L.; Vedso, P.; Begtrup, M. J. Org. Chem., 2003, 68, 4091.
80. Hormi, O.E.O.; Hirvela, L. Tetrahedron Lett., 1993, 34, 6463.
81. Martin, N.H.; Clary, R.T.; Fudala, L.D.; Hyde, R.G.; Jackson, E.P.; Vehling, J.M.; O'Conner, F.; Pennington, G.A.; Piner, R.T. J. Elisha Mitchell Sci. Soc., 1992, 108, 102.
82. Suau, R.; Rico, R.; López-Romero, J.M.; Nájera, F.; Ruiz, A.; Ortiz-López, F.J. Arkivoc, 2002, 62.
83. Simoneau, B.; Brassard, P. J. Chem. Soc. Perkin Trans. 1, 1984, 1507.
84. Bode, J.W.; Hachisu, Y.; Matsuura, T.; Suzuki, K. Org. Lett., 2003, 5, 391.
85. Chandrasekhar, B.; Ramadas, S.R.; Ramana, D.V. Tetrahedron, 2000, 56, 5947.
86. Casillas, L.K.; Townsend, C.A. J. Org. Chem., 1999, 64, 4050.
87. Udwary, D.W.; Casillas, L.K.; Townsend, C.A. J. Am. Chem. Soc., 2002, 124, 5294.
88. Shaabani, A.; Mirzaei; P.; Naderia, S.; Lee, D.G. Tetrahedron, 2004, 60, 11415.
89. Shaabani, A.; Bazgir, A.; Teimouria, F.; Lee, D.G. Tetrahedron Lett., 2002, 43, 5165.
90. Bryant, J.R.; Mayer J.M. J. Am. Chem. Soc., 2003, 125, 10351.
91. Shaabania, A.; Lee, D.G. Tetrahedron Lett., 2001, 42, 5833.
92. Terao, Y.; Nomoto, M.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem., 2003, 68, 5236.
93. Ghosh, C.K.; Gosh, C. Indian J. Chem., 1997, 36B, 968.
94. Ghosh, C.K.; Bhattacharyya, A.; Bandyopadhyay C. J. Chem. Soc. Chem. Commun., 1984, 1319.
95. Ghosh, C.K.; Sahana, S.; Patra, A. Tetrahedron, 1993, 49, 4127.
96. Ghosh, C.K.; Bhattacharyya, S.; Ghosh, C.; Patra, A. J. Chem Soc. Perkin Trans. 1, 1999, 3005.
97. Ghosh, C.K.; Bhattacharyya, S.; Patra, A. J. Chem. Soc. Perkin Trans. 1, 1997, 15, 2167.
98. Kelkar, A.S.; Letcher, R.M.; Cheung, K.-K.; Chiu, K.-F.; Brown, G.D. J. Chem. Soc. Perkin Trans. 1, 2000, 3732.
99. Daia, G.E.; Gabbutt, C.D.; Hepworth, J.D.; Heron, B.M.; Hibbs, D.E.; Hursthouse, M.B. Tetrahedron Lett., 2002, 43, 4507.
100. Gabbutt, C.D.; John D.; Urquhart, M.W.J.; Vazquez, L.M.-M. J. Chem. Soc. Perkin Trans. 1, 1997, 1819.
101. Xu, F.; Cao, X.; Cao, Z.; Zou, L. Tetrahedron Lett., 2000, 41, 10257.
102. Lesch, B.; Brase, S. Angew. Chem. Int. Ed., 2004, 43, 115.
103. Aida, M.; Yamagami, Y.; Hano, Y.; Noruma, T. Heterocycles, 1996, 43, 2561.
104. Prashad, M.; Lu, Y.; Repic, O. J. Org. Chem., 2004, 69, 584.
105. Burdette, S.C.; Frederickson, C.J.; Bu, W.; Lippard, S.J. J. Am. Chem. Soc., 2003, 125, 1778.
106. Kaiser, F.; Schmalz, H.-G. Tetrahedron, 2003, 59, 7345.
107. Cooney, J.M.; Gommans, L.H.P.; Main, L.; Nicholson, B.K. J. Organometallic Chem., 2001, 634, 157.
108. Kostakis, I.K.; Pouli, N.; Marakos, P.; Mikros, E.; Skaltsounis, A.L.; Leonce, S.; Atassi, G.; Renard, P. Bioorg. Med. Chem., 2001, 9, 2793.
109. Turk, A.; Plé, N.; Tallon, V.; Queguiner, G. Tetrahedron, 1995, 51, 13045.
110. Kristensen, J.L.; Vedso, P.; Begtrup, M. Tetrahedron, 2002, 2397.
111. Fujiwara, H.; Kitagawa, K. Chem. Pharm. Bull., 2000, 48, 1380.
112. Recanatini, M.; Bisi, A.; Cavalli, A.; Belluti, F.; Gobbi, S.; Rampa, A.; Valenti, P.; Palzer, M.; Palusczak, A.; Hartmann, R.W. J. Med. Chem., 2001, 44, 672.
113. Szajnman, S.H.; Yan, W.; Bailey, B.N.; Docampo, R.; Elhalem, E.; Rodriguez, J.B. J. Med. Chem., 2000, 43, 1826.
114. Re, P. D.; Valenti, P.; Borraccini, A.; Primofiore, G.P. J. Med. Chem., 1972, 15, 198.
115. García, A.; Domínguez, D. Tetrahedron Lett., 2001, 42, 5219.
116. Rewcastle, G.W.; Atwell, G.J.; Li, Z.A.; Baguley, B.C.; Denny, W.A. J. Med. Chem., 1991, 34, 217.
117. Gobbi, S.; Rampa, A.; Bisi, A.; Bellutti, F.; Valenti, P.; Caputo, A.; Zampiron, A.; Carrara, M. J. Med. Chem., 2002, 45, 4931.
118. Kelly, J.X.; Winter, R.; Peyton, D.H.; Hinrichs, D.J.; Riscoe, M. Antimicrob. Agents Chemother., 2002, 46, 144.
119. Kelly, J.; Winter, R.; Cornea, A.; Peyton, D.; Hinrichs, D.; Riscoe, M. Mol. Biochem. Parasitol., 2002, 123, 47.
120. Valenti, P.; Chiarini, A.; Gasperi, F.; Budriesi, R. Arzneim.-Forsch./Drug. Res., 1990, 40, 122.
121. Fernandes, E.G.R.; Silva, A.M.S.; Cavaleiro, J.A.S.; Silva, F.M.; Borges, M.F.M.; Pinto, M.M. Magn. Reson. Chem., 1998, 36, 305.
122. Wang, T.C.; Zhao, Y.-L.; Liou, S.-S. Helv. Chim. Acta, 2002, 85, 1382.
123. Rampa, A.; Bisi, A.; Valenti, P.; Recanatini, M.; Cavalli, A.; Andrisano, V.; Cavrini, V.; Fin, L.; Buruani, A.; Giusti, P. J. Med. Chem., 1998, 41, 3976.
124. Jastrzebska-Wiesek, M.; Librowski, T.; Czarnecki, R.; Marona, H.; Nowak, G. Pol. J. Pharmacol., 2003, 55, 461.
125. Marona, H. Pharmazie, 1998, 53, 672.
126. Marona, H. Pharmazie, 1998, 53, 405.
127. Marona, H.; Gorka, Z.; Szneler, E. Pharmazie, 1998, 53, 219.
128. Marona, H.; Pekala, E.; Filipek, B.; Maciag, D.; Szneler, E. Pharmazie, 2001, 56, 567.
129. Librowski, T.; Czarnecki, R.; Jastrzebska, M. Acta Pol Pharm., 1999, 56, 87.
130. Marona, H.; Szneler, E.; Filipek, B.; Sapa, J. Acta Pol. Pharm., 1997, 54, 63.
131. Bisi, A.; Budriesi, R.; Rampa, A.; Fabbri, G.; Chiarini, A.; Valenti, P. Arzneim.-Forsch./Drug. Res., 1996, 46, 848.
132. Rampa, A.; Chiarini, A.; Bisi, A.; Budriesi, R.; Valenti, P. Arzneim.-Forsch./Drug. Res., 1991, 41, 705.
133. Wang, L.W.; Kang, J.J.; Chen, I.J.; Teng, C.M.; Lin, C.N. Bioorg. Med. Chem., 2002, 10, 567.
134. Pifferi, G.; Re, P. D.; Valenti, P.; Bisi, A.; Malandrino, S. Arch. Pharm. (Weinheim.), 1997, 330, 233.
135. Chen, Y.-L.; Chen, P.-H.; Chung, C.-H.; Li, K.C.; Jeng, H.-Y.; Tzeng, C.-C. Helv. Chim. Acta, 2003, 86, 778.
136. Kostakis, I.K.; Ghirtis, K.; Pouli, N.; Marakos, P.; Skaltsounis, A.L.; Leonce, S.; Gaignard, D.H.; Atassi, G. Farmaco, 2000, 55, 455.
137. Chen, Y.-L.; Chen, I.-L.; Tzeng, C.-C. Helv. Chim. Acta, 2000, 83, 989.
138. Pickets M.; Frahm, W.A. Arch. Pharm., 1998, 177.
139. Rewcastle, G.W.; Atwell, G.J.; Baguley, B.C.; Calveley, S.B.; Denny, W.A. J. Med. Chem., 1989, 32, 793.
140. Hernandez, J.V.; Muniz, F.M.; Oliva, A.I.; Simon, L.; Perez, E.; Moran, J.R. Tetrahedron Lett., 2003, 44, 6983.
141. Pfister, J.R.; Ferraresi, R.W.; Harrison, I.T.; Rooks, W.H.; Roszkowski, A.P.; Van Horn, A.; Fried, J.H. J. Med. Chem., 1972, 15, 1032.
142. Patel, G.N.; Verma, R.S.; Pardasani, R.T.; Trivedi, K.N. Polish J. Chem., 1988, 62, 409.
143. Thull, U.; Kneubuhler, S.; Testa, B.; Borges, M.F.; Pinto, M.M. Pharm. Res., 1993, 10, 1187.
144. Pinto, M.M.M.; Polónia, J. Helv. Chim. Acta, 1974, 57, 2613.
145. Heald, R.A.; Dexheimer, T.S.; Vankayalapati, H.; Siddiqui-Jain, A.; Szabo, L.Z.; Gleason-Guzman, M.C.; Hurley, L.H. J. Med. Chem., 2005, 48, 2993.
146. Lown, J.W.; Sondhi, S.M. J. Org. Chem., 1985, 50, 1413.
147. Essery, J.M.; O'Herron, F.A.; McGregor, D.N.; Bradner, W.T. J. Med. Chem., 1976, 19, 1339.
148. Bhat, H.B.; Venkataraman, K. Tetrahedron, 1963, 19, 77.
149. Lewis, J.R.; Reary, J.B. J. Chem. Soc. C, 1970, 1622.
150. Schneider, J.; Evans, E.L.; Grunberg, E.; Fryer, R.I. J. Med. Chem., 1972, 266.
151. Helesbeux, J.-J.; Duval, O.; Dartiguelongue, C.; Seraphin, D.; Oger, J.-M.; Richomme, P. Tetrahedron, 2004, 60, 2293.
152. Kondedesshmukh, R.S.; Paradkar, M.V. Synthetic Commun., 1994, 24, 659.
153. Sun, L.; Liebeskind, L.S. Tetrahedron Lett., 1997, 38, 3663.
154. Sun, L.; Liebeskind, L.S. J. Am. Chem. Soc., 1996, 118, 12473.
155. Letcher, R.M.; Yue, T.-Y.; Chiu, K.-F.; Kelkar, A.S.; Cheung, K.-K. J. Chem. Soc. Perkin Trans. 1, 1998, 3267.
156. Pinto, M.M.M.; Sousa, E.P. Curr. Med. Chem., 2003, 10, 1.
157. Sandulache, A.; Silva, A.M.S.; Cavaleiro, J.A.S. Monatsh. Chem., 2003, 134, 551.
158. Kolokythas, G.; Kostakis, I.K.; Pouli, N.; Marakos, P.; Skaltsounis, A.-L.; Pratsinis, H. Bioorg. Med. Chem. Lett., 2002, 12, 1443.
159. Sandulache, A.; Silva, A.M.S.; Cavaleiro, J.A.S. Tetrahedron, 2002, 58, 105.
160. Silva, A.M.S.; Pinto, D.C.G.A.; Tavares, H.R.; Cavaleiro, J.A.S.; Jimeno, M.L.; Elguero, J. Eur. J. Org. Chem., 1998, 2031.
161. Kim, S.S.; Lim, C.H.; Yoo, D.Y.; Joong, K.; Ahn, B.J.; Schim, S.C. Bull. Korean Chem. Soc., 1993; 14, 661.
162. Hauser, F.M.; Piyasenna, H.; Baghdanov, V.M. J. Org. Chem., 1988, 53, 223.
163. Hauser, F.M.; Dorsch, W.A. Org. Lett., 2003, 5, 3753.
164. Croisy-Delcey, M.; Croisy, A.; Mousset, S.; Letourneur, M.; Bisagni, E.; Jacquemin-Sablon, A.; Pierre, J. Biomed. Pharmacother., 1997, 51, 286.
165. Pengsuparp, T.; Cai, L.; Constant, H.; Fong, H.H.; Lin, L.Z.; Kinghorn, A.D.; Pezzuto, J.M.; Cordell, G.A.; Ingolfsdottir, K.; Wagner, H. J. Nat. Prod., 1995, 58, 1024.
166. Nising, C.F.; Schmid, U.K.; Nieger, M.; Bräse, S. J. Org. Chem., 2004, 69, 6830.
167. Colquhoun, H.M.; Lewis, D.F.; Williams, D.J. Org. Lett., 2001, 3, 2337.
168. Okawa, H.; Yoshino, T. Bull Chem. Soc. Japan, 1970, 805.
169. Agbaria, K.; Biali, S.E. J. Org. Chem., 2001, 66, 5482.
170. Hernandez, J.V.; Oliva, A.I.; Simon, L.; Muniz, F.M.; Grande, M.; Moran, J.R. Tetrahedron Lett., 2004, 45, 4831.
171. Mills, O.S.; Mooney, N.J.; Robinson, P.M.; Watt, C.I.F.; Box, B.G. J. Chem. Soc. Perkin Trans. 2, 1995, 697.
172. Beddoes, R.S.; Cox, B.G.; Mills, O.S.; Mooney, N.J.; Watt, C.I.F.; Kirkland, D.; Martin, D. J. Chem. Soc. Perkin Trans. 2, 1996, 2, 2091.
173. Krieger, F.; Fierz, B.; Bieri, O.; Drewello, M.; Kiefhaber, T. J. Mol. Biol., 2003, 332, 265.
174. Gil, S.; Parra, M.; Sanz, V.; Tortajada, A. J. Nat. Prod., 1988, 51, 339.
175. Bennet, G.J.; Lee, H.-H.; Lee, L.-P. J. Nat. Prod., 1990, 53, 1463.
176. Gil, S.; Palanca, P.; Sanz, V.; Tortajada, A. J. Nat. Prod., 1991, 54, 127.
177. Nicolaou, K.C.; Sasmal, P.K.; Xu, H. J. Am. Chem. Soc., 2004, 126, 5493.
178. Tisdale, E.J.; Li, H.; Vong, B.G.; Kim, S.H.; Theodorakis, E.A. Org. Lett., 2003, 5, 1491.
179. Tisdale, E.J.; Chowdhury, C.; Vong, B. G.; Li, H.; Theodorakis, E.A. Org. Lett., 2002, 4, 909.
180. Kim, M.Y.; Na, Y.; Vankayalapati, H.; Gleason-Guzman, M.; Hurley, L.H. J. Med. Chem., 2003, 46, 2958.
181. Piettre, A.; Chevenier, E.; Massardier, C.; Gimbert, Y.; Greene. A.E. Org. Lett., 2002, 4, 3139.
182. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem., 1978, 49, 3671.
183. Ahluwalia, V.K.; Tehim, A.K. Tetrahedron, 1984, 40, 3303.
184. Tisdale, E.J.; Slobodov, I.; Theodorakis, E.A. Org. Biomol. Chem., 2003, 4418.
185. Perrin, R.; Muyard, F.; Bévalot, F.; Tillequin, F.; Vaquette, J. J. Nat. Prod., 2000, 63, 245.
186. Subba-Rao, G.S.R. Pure Appl. Chem., 2003, 75, 1443.
187. Tisdale, E.J.; Kochman, D.A.; Theodorakis, E.A. Tetrahedron Lett., 2003, 44, 3281.
188. Habib, A.M.; Ho, D.K.; Masuda, S.; McCloud, T.; Reddy, K.S.; Aboushoer, M.; McKenzie, A.; Byrn, S.R.; Chang, C.-J.; Cassady, J.M. J. Org. Chem., 1987, 52, 412.
189. Terrance, T.; Schwaebe, M.K.; Whitten, J.P. W.O. Patent 2004/019888, 2004.
190. About the Progress Towards the Total Synthesis of Psorospermin: Synthesis of Psorospermin Methyl Ether, URL http://www.albmolecular.com/features/tekreps/vo104/no48 (accessed May 2005).
191. Scannell, R.T.; Stevenson, R. J. Heterocyclic Chem., 1986, 23, 857.
192. Mehta, G.; Shah, S. R.; Venkateswarlu, Y. Tetrahedron 1994, 50, 11729.
193. Mehta, G.; Shah, S.R. Tetrahedron Lett. 1991, 32, 5195.
194. Kang, J.-J.; Fang, H.-W. Biochem. Biophys. Res. Comm., 1997, 238, 367.
195. Fuente, M.C.; Dominguez, D. Tetrahedron, 2004, 60, 10019.
196. Chen, C.A.; Yeh, R.H.; Lawrence, D.S. J. Am. Chem. Soc., 2002, 124, 3840.
197. Urano, Y.; Kamiya, M.; Kanda, K.; Ueno, T.; Hirose, K.; Nagano, T. J. Am. Chem. Soc., 2005, 127, 4888.
198. Martin, J.A.; Lambert, R.W.; Merrett, J.H.; Parkes, K.E.B.; Thomas; G.J., Baker, S.J.; Bushnell, D.J.; Cansfield, J.E.; Dunsdon S.J.; Freeman, A.C.; Hopkins, R.A.; Johns, I.R.; Keech, E.; Simmonite, H.; Walmsley, A.; Kai-In, P.W.; Holland, M. Bioorg. Med. Chem., 2001, 11, 1655.
199. Kwan, M.L.; Battiste, M.A. Tetrahedron Lett., 2002, 43, 8765.
200. Henkel, B.; Zeng W.; Bayer, E. Tetrahedron Lett., 1997, 38,3511.
201. Aubin, L.B.; Wagner, T.M.; Thoburn, J.D.; Kesler, B.S., Hutchison, K.A.; Schumaker, R.R., Parakka, J.P. Org. Lett., 2001, 3, 3413.
202. Reese, C.B.; Yan, H. J. Chem. Soc. Perkin Trans. 1, 2001, 15, 1807.
203. Nilsson, J.P.; Andersson, C.-M. Tetrahedron Lett., 1997, 38, 4635.
204. Hekmatshoar, R.; Yavari, I.; Beheshtiha, Y.S.; Heravi, M.M. Monatsh. Chem. 2001, 132, 689.
205. Donovan, P.M.; Scott, L.T. J. Am. Chem. Soc., 2004, 126, 3108.
206. About the GPI 6150 a Novel PARP Inhibitor, is Cardioprotective and Neuroprotective in Rat Models of Ischemia, U R L http://www.albmolecular.com/features/tekreps/vol04/no48 (accessed May 2005).
207. Wechter, W. J. J. Org. Chem., 1963, 28, 2935.
208. Halton, B.; Cooney, M. J.; Boese, R.; Maulitz, A. H. J. Org. Chem., 1998, 63, 1583.
209. Martin, J. C.; Smith, R. G. J. Am. Chem. Soc., 1964, 86, 2252.
210. Song, J.-S.; Szalda, D.J.; Bullock, R.M. Organometallics, 2001, 20, 3337.
211. Mulder, P.; Hemmink, S.; Heer, M.I.; Lupo, M.; Santoro, D.; Korth, H.-G. J. Org. Chem., 2001, 66, 6611.
212. Lin, Q.; Leong, W.K. Organometallics, 2003, 22, 3639.