α-Amino acids and derivatives in the asymmetric synthesis of tetrahydroisoquinoline alkaloids

Current Organic Chemistry

Volumn 7, Issue 18, 2003, Pages 1775-1792

  Vicario, Jose L ^a   Badía, Dolores ^a   Carrillo, Luisa ^a   Extebarria, Juan ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIHYDROISOQUINOLINE DERIVATIVE; 3 METHYL 1,2,3,4 TETRAHYDROISOQUINOLIN 1 ONE; ALPHA AMINO ACID; AMINO ACID DERIVATIVE; AMURENSININE; ARGEMONINE; CORLUMINE; CRYPTOSTYLINE I; CRYPTOSTYLINE II; CURLUMINE; HOMOLAUDANOSINE; IMBRICATINE; ISOPAVINE DERIVATIVE; ISOQUINOLINE ALKALOID; LAUDANOSINE; LEVORPHANOL; NATURAL PRODUCT; NORARMEPAVINE; NORCRYPTOSTYLINE III; O METHYLTHALISOPAVINE; PODOPHYLLOTOXIN; RETICULINE; SALSOLIDINE; TETRAHYDROIMIDAZO[1,5 B]ISOQUINOLIN 1(5H) ONE DERIVATIVE; TETRAHYDROISOQUINOLINE; TETRAHYDROISOQUINOLINE DERIVATIVE; TETRAZOMINE; TRETOQUINOL; UNCLASSIFIED DRUG; UNINDEXED DRUG; XYLOPININE;

ASYMMETRIC SYNTHESIS; CHIRALITY; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; PHYSICAL CHEMISTRY; REVIEW; STEREOCHEMISTRY;

EID: 0344899921     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272033486143     Document Type: Review

References (155)

1. (a) The Isoquinoline Alkaloids, Chemistry and Pharmacology; Shamma, M. Ed.; Academic Press: New York, 1972.
2. (b) The Chemistry and Biology of Isoquinoline Alkaloids; Philipson, J. D.; Roberts, M. F.; Zenk, M. H. Eds; Springer-Verlag: New York, 1985.
3. For a review: Bentley, K. W. Nat. Prod. Rep. 2001, 18, 148.
4. Crosby, J. Tetrahedron 1991, 47, 4789.
5. For previous reviews see (a) Rozwadowska, M. D. Heterocycles 1994, 39, 903.
6. (b) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
7. For a review on Pictet-Spengler cyclization see Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
8. (a) Larsen, R. D.; Reamer, R. A.; Corley, E. G.; Davis, P.; Grabowski, E. J. J.; Reider, P. J.; Shinkai, I. J. Org. Chem. 1991, 56, 6034.
9. (b) Venkov, A. P.; Ivanov, I. I. Tetrahedron 1996, 52, 12299.
10. (a) Gensler, W. J. Org. React. 1951, 6, 191.
11. (b) Bobbit, J. M.; Roy, D. N.; Marchand, A.; Allen, C. W. J. Org. Chem. 1967, 32, 2225.
12. (c) Simig, G.; Schlosser, M. Tetrahedron Lett. 1990, 31, 3125.
13. (a) Bates, H. A. J. Org. Chem. 1981, 46, 4931.
14. (b) Bates, H. A. J. Org. Chem. 1983, 48, 1932.
15. Coote, S. J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1988, 648.
16. Coote, S. J.; Davies, S. G. J. Chem. Soc., Perkin Trans. 1 1989, 2223.
17. Bròzda, D.; Koroniak, L.; Rozwadowska, M. D. Tetrahedron: Asymmetry 2000, 11, 3017.
18. Chandrasekhar, S.; Reddy, N. R.; Reddy, M. V.; Jagannadh, B.; Nagaraju, A.; Sankar, A. R.; Kunwar, A. C. Tetrahedron Lett. 2002, 43, 1885.
19. (a) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 30, 2198.
20. (b) Reetz, M. T.; Dreves, M. W. Angew. Chem. Int. Ed. Engl. 1987, 26, 1141.
21. (c) Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709.
22. Wipf, P.; Hopkins, C. R. J. Org. Chem. 2001, 66, 3133.
23. (a) Sato, T.; Hirayama, F.; Saito, T. J. Antibiot. 1991, 44, 1367.
24. (b) Suzuki, K.; Sato, T.; Morioka, M.; Nagai, K.; Abe, K.; Yamaguchi, H.; Saito, T.; Ohmi, Y.; Susaki, K. J. Antibiot. 1991, 44, 479.
25. (c) Williams, R. M.; Flanagan, M. E.; Tippie, T. N. Biochemistry 1994, 33, 4086.
26. Hirsenkorn, R. Tetrahedron Lett. 1990, 31, 7591.
27. (a) Dyke, S. F. Tetrahedron 1971, 27, 3803.
28. (b) Elliott, R.; Hewgill, F.; McDonald, E.; McKenna, P. Tetrahedron Lett. 1980, 21, 4633.
29. Hirsenkorn, R. Tetrahedron Lett. 1991, 32, 1775.
30. Carrillo, L.; Badía, D.; Domínguez, E.; Vicario, J. L.; Tellitu, I. J. Org. Chem. 1997, 62, 6716.
31. The observed behavior can be explained by assuming that the process involves two sequential electrophilic cyclizations probably through a 1-benzyltetrahydroisoquinoline intermediate (see ref. [21]).
32. Dyke, S. F.; Ellis, A. C.; Kinsman, R. G.; White, A. W. C. Tetrahedron 1974, 30, 1193.
33. Hanessian, S.; Mauduit, M. Angew. Chem. Int. Ed. Engl. 2001, 40, 3810.
34. For a review on Stevens rearrangements see Markó, I. E. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Pattenden I., Eds.; Pergamon: Oxford, 1991; Vol. 3, p. 913.
35. Schultz, A. G.; Guzi, T. J.; Larsson, E.; Rahm, R.; Thakkar, K.; Bidlack, J. M. J. Org. Chem. 1998, 63, 7795.
36. Eaton, P.; Carlson, G. R.; Lee, J. T. J. Org. Chem. 1973, 38, 4071.
37. Hayashi, K.; Ozaki, Y.; Nunami, K.-I.; Yoneda, N. Chem. Pharm. Bull. 1983, 31, 312.
38. Manini, P.; D'Ischia, M.; Prota, G. J. Org. Chem. 2001, 66, 5048.
39. Spengler, J.; Schedel, H.; Sieler, J.; Quaedflieg, P. J. L. M.; Broxterman, Q. B.; Duchateau, A. L. L.; Burger, K. Synthesis 2001, 1513.
40. (a) Allin, S. M.; James, S. L.; Martin, W. P.; Smith, T. A. D. Tetrahedron Lett. 2001, 42, 3943.
41. (b) Allin, S. M.; Vaidya, D. G.; James, S. L.; Allard, J. E.; Smith, T. A. D.; McKee, V.; Martin, W. P. Tetrahedron Lett. 2002, 43, 3661.
42. Katritzky, A.R.; Cobo-Domingo, J.; Yang, B.; Steel, P. J. Tetrahedron: Asymmetry 1999, 10, 255.
43. Katritzky, A. R.; He, H.-Y.; Jiang, R.; Long, Q. Tetrahedron: Asymmetry 2001, 12, 2427.
44. Katritzky, A. R.; Suzuki, K.; He, H.-Y. J. Org. Chem. 2002, 67, 8224.
45. Huber, I. M. P.; Seebach, D.; Syfrig, M. A. Helv. Chim. Acta 1987, 70, 1357.
46. Huber, I. M. P.; Seebach, D. Helv. Chim. Acta 1987, 70, 1944.
47. This derivative was prepared from (S)-DOPA, according to a patent: Hoefle, M. L.; Klutchko, S. to Warner-Lambert Company. U.S. Patent 4,344,949, 1982.
48. Monsees, A.; Laschat, S.; Dix, I. J. Org. Chem. 1998, 63, 10018.
49. Yamaguchi, R.; Hamasaki, T.; Ohta, T.; Utimoto, K.; Kozima, S.; Takaya, H. J. Org. Chem. 1993, 58, 1136.
50. Haraguchi, Y.; Kozima, S.; Yamaguchi, R. Tetrahedron: Asymmetry 1996, 7, 443.
51. O'Reilly, N. J.; Derwin, W. S.; Lin, H. C. Synthesis 1990, 550.
52. Garcia, E.; Arrasate, S.; Ardeo, A.; Lete, E.; Sotomayor, N. Tetrahedron Lett. 2001, 42, 1511.
53. Ohba, M.; Nishimura, Y.; Kato, M.; Fujii, T. Tetrahedron 1999, 55, 4999.
54. (a) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 65.
55. (b) Schöllkopf, U. Pure Appl. Chem. 1983, 55, 1799.
56. Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716.
57. (a) Yamato, M.; Hashigaki, K.; Ishikawa, S.; Qais, N. Tetrahedron Lett. 1988, 29, 6949.
58. (b) Hashigaki, K.; Ishikawa, S.; Wan, W.; Yamato, M. Synthesis 1988, 1001.
59. (c) Yamato, M.; Hashigaki, K.; Qais, N.; Ishikawa, S. Tetrahedron 1990, 46, 5909.
60. Amat, M.; Canto, M.; Llor, N.; Escolano, C.; Molins, E.; Espinosa, C.; Bosch, J. J. Org. Chem. 2002, 67, 5343 and refs. therein.
61. Hashigaki, K.; Kan, K.; Qais, N.; Takeuchi, Y.; Yamato, Y. Chem. Pharm. Bull. 1991, 39, 1126.
62. Carbonnelle, A.-C.; Gott, V.; Roussi, G. Heterocycles 1993, 36, 1763.
63. Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 6709.
64. Yamazaki, N.; Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1996, 37, 6161.
65. Carrillo, L.; Badía, D.; Domínguez, E.; Anakabe, E.; Osante, I.; Tellitu, I.; Vicario, J. L. J. Org. Chem. 1999, 64, 1115.
66. (a) Ungemach, F.; DiPierro, M.; Weber, R.; Cook, J. M. J. Org. Chem. 1981, 46, 164.
67. (b) Domínguez, E.; Lete, E.; Badía, D.; Villa, M. J.; Castedo, L.; Domínguez, D. Tetrahedron 1987, 43, 1943.
68. Bringmann, G.; Weirich, R.; Reuscher, H.; Jansen, J. R.; Kinzinger, L.; Ortmann, T. Liebigs Ann. Chem. 1993, 877.
69. Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron 1994, 50, 1083.
70. (a) Comins, D. L.; Badawi, M. M. Heterocycles 1991, 32, 1869.
71. (b) Barbier, D.; Marazano, C.; Das, B. C.; Potier, P. J. Org. Chem. 1996, 61, 9596.
72. Barbier, D.; Marazano, C.; Riche, C.; Das, B. C.; Potier, P. J. Org. Chem. 1998, 63, 1767.
73. Cabedo, N.; Andreu, I.; Ramírez de Arellano, M. C.; Chagraoui, A.; Serrano, A.; Bermejo, A.; Portáis, P.; Cortes, D. J. Med. Chem. 2001, 44, 1794.
74. For a recent review see Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843.
75. Munchoff, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7086.
76. Munchoff, M. J.; Meyers, A. I. J. Org. Chem. 1996, 61, 4607.
77. a) Royer, J.; Husson, H.-P. Janssen Chim. Acta 1993, 36, 468.
78. (b) Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383.
79. Gosmann, G.; Guillaume, D.; Husson, H.-P. Tetrahedron Lett. 1996, 37, 4396.
80. Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475.
81. Lienard, P.; Quirion, J.-C.; Husson, H.-P. Tetrahedron 1993, 49, 3995.
82. Pedrosa, R.; Andrés, C.; Iglesias, J. M. J. Org. Chem. 2001, 66, 243.
83. Pedrosa, R.; Andres, C.; Iglesias, J. M.; Pérez-Encabo, A. J. Am. Chem. Soc. 2001, 123, 1817.
84. (a) Micouin, L.; Varea, T.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2529.
85. (b) Shanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533.
86. (c) Amat, M.; Llor, N.; Hidalgo, J.; Hernández, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977.
87. Philippe, N.; Levacher, V.; Dupas, G.; Duflos, J.; Quéguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1996; 7, 417.
88. Roussi, F.; Quirion, J.-C.; Tomas, A.; Husson, H.-P. Tetrahedron 1998, 54, 10363.
89. Philippe, N.; Levacher, V.; Dupas, G.; Quéguiner, G.; Bourguignon, J. J. Org. Lett. 2000, 2, 2185.
90. Jullian, V.; Quirion, J.-C.; Husson, H.-P. Synthesis 1997, 1091.
91. Jullian, V.; Quirion, J.-C.; Husson, H.-P. Eur J. Org. Chem. 2000, 1319.
92. Alezra, V.; Bonin, M.; Micouin, L.; Husson, H.-P. Tetrahedron Lett. 2001, 42, 2111.
93. Vicario, J. L.; Badía, D.; Domínguez, E.; Carrillo, L. Tetrahedron: Asymmetry 2000, 11, 3779.
94. (a) Méa-Jacheet, D.; Horeau, A. Bull. Soc. Chim. Fr. 1968, 4571.
95. (b) Kitamoto, M.; Hirai, K.; Terashima, S.; Yamada, S.-I. Chem. Pharm. Bull. 1974, 22, 459.
96. (c) Meyers, A. I.; Williams, D. R.; Druelinger, M. J. Am. Chem. Soc. 1976, 98, 3032.
97. (d) Whitesell, J. K.; Whitesell, M. A. J. Org. Chem. 1977, 42, 377.
98. (e) Hashimoto, S.; Koga, K. Tetrahedron Lett. 1978, 19, 573.
99. (f) Meyers, A. I.; Poindexter, G. S.; Brich, Z. J. Org. Chem. 1978, 43, 892.
100. (g) Meyers, A. I.; Williams, D. R. J. Org. Chem. 1978, 43, 3245.
101. (h) Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253.
102. Zaragoza, F. Synlett 1995, 237.
103. (a) West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1994, 116, 8420.
104. (b) West, F. G.; Naidu, B. N. J. Org. Chem. 1994, 59, 6051.
105. Hanessian, S.; Demont, E.; Van Otterlo, W. A. L. Tetrahedron Lett. 2000, 41, 4999.
106. (a) Jako, I.; Uiber, P.; Mann, A.; Taddei, M.; Wermuth, C.-G. Tetrahedron Lett. 1990, 31, 1011.
107. (b) Hanessian, S.; Sumi, K. Synthesis 1991, 1083.
108. (c) Hanessian, S.; Wang, W.; Gai, Y. Tetrahedron Lett. 1996, 37, 7477.
109. Falz, H.; Radspieler, A.; Liebscher, J. Synlett 1997, 1071.
110. (a) Tietze, L. F.; Burkhardt, O. Synthesis 1994, 1331.
111. (b) Tietze, L. F.; Burkhardt, O.; Henrich, M. Liebigs Ann. 1997, 1407.
112. (a) Kazmiersky, W. M.; Hruby, V. J. Tetrahedron Lett. 1991, 32, 5769.
113. (b) Kazmiersky, W. M.; Urbanczyk-Lipkowska, Z.; Hruby, V. J. J. Org. Chem. 1994, 59, 1789.
114. Zhang, N.; Nubbemeyer, U. Synthesis, 2002, 242.
115. Zawadzka, A.; Leniewski, A.; Maurin, J. K.; Wijtasiewicz, K.; Czarnocki, Z. Org. Lett. 2001, 3, 997.
116. Chandrasekhar, S.; Mohanty, P. K.; Harikishan, K.; Sasmal, P. K. Org. Lett. 1999, 1, 877-878.
117. (a) Carillo, L.; Badía, D.; Domínguez, E.; Ortega, F.; Tellitu, I. Tetrahedron: Asymmetry 1998, 9, 151.
118. (b) Vicario, J. L.; Badía, D.; Carrillo, L.; Anakabe, E. Tetrahedron: Asymmetry 2003, 14, 347.
119. (a) Vicario, J. L.; Badía, D.; Dominguez, E.; Crespo, A.; Carrillo, L.; Anakabe, E. Tetrahedron Lett. 1999, 40, 7123.
120. (b) Anakabe, E.; Vicario, J. L.; Badía, D.; Carrillo, L.; Yoldi, V. Eur. J. Org. Chem. 2001, 4343.
121. Tellitu, I.; Badía, D.; Domínguez, E.; García, F. J. Tetrahedron: Asymmetry 1994, 5, 1567.
122. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B. Tetrahedron: Asymmetry 1993, 4, 273.
123. Kita, Y.; Takada, T.; Gyoten, M.; Toma, H.; Zenk, M. H.; Eichorn, J. J. Org. Chem. 1996; 61, 5857.
124. (a) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley & Sons: New York, 1995.
125. (b) Studer, A. Synthesis 1996, 793.
126. (c) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
127. (a) Meyers, A. I.; Fuentes, L. M. J. Am. Chem. Soc. 1983, 105, 117.
128. (b) Meyers, A. I.; Boes, M.; Dickman, D. A. Angew. Chem. Int. Ed. Engl. 1984, 23, 458.
129. (c) Meyers, A. I.; Miller, D.; White, F. J. Am. Chem. Soc. 1988, 110, 4778.
130. (d) Meyers, A. I. Tetrahedron 1992, 48, 2589.
131. (a) Loewe, M. F.; Boes, M.; Meyers, A. I. Tetrahedron Lett. 1985, 26, 3925.
132. (b) Meyers, A. I.; Dickman, D. A. J. Am. Chem. Soc. 1987, 109, 1263.
133. (c) Castonguay, L. A.; Guiles, J. W.; Rappé, A. K.; Meyers, A. I. J. Org. Chem. 1992, 57, 3819.
134. (d) Meyers, A. I.; Warmus, J. S.; Gonzalez, M. A.; Guiles, J.; Akahane, A. Tetrahedron Lett. 1991, 32, 5509.
135. Meyers, A. I.; Dickman, D. A.; Boes, M. Tetrahedron 1987, 43, 5095.
136. Meyers, A. I.; Guiles, J. Heterocycles 1989, 28, 295.
137. Dickman, D. A.; Meyers, A. I. Tetrahedron Lett. 1986, 27, 1465.
138. Gottlieb, L.; Meyers, A. I. J. Org. Chem. 1990, 55, 5659.
139. Matulenko, M. A.; Meyers, A. I. J. Org. Chem. 1996, 61, 573.
140. Guiles, J. W.; Meyers, A. I. J. Org. Chem. 1991, 56, 6873.
141. Cutter, P. S.; Miller, R. B.; Schore, N. E. Tetrahedron 2002, 58, 1471.
142. Itoh, T.; Nagata, K.; Miyazaki, M.; Ohsawa, A. Synlett 1999, 1154.
143. Itoh, T.; Nagata, K.; Miyazaki, M.; Kameoka, K.; Ohsawa, A. Tetrahedron 2001, 57, 8827.
144. Vicario, J. L.; Badía, D.; Domínguez, E.; Carrillo, L. J. Org. Chem. 1999, 64, 4610.
145. Sotomayor, N.; Vicente, T.; Domínguez, E.; Lete, E.; Villa, M.-J. Tetrahedron, 1994, 50, 2207.
146. Vicario; J. L.; Badía, D.; Domínguez, E.; Crespo, A.; Carrillo, L. Tetrahedron: Asymmetry 1999, 10, 1947.
147. Vicario, J. L.; Badía, D.; Domínguez, E.; Carrillo, L. Tetrahedron: Asymmetry 2000, 11, 1227.
148. (a) Denmark, S. E.; Nicaise, O. J. C. J. Chem. Soc., Chem. Commun. 1996, 999.
149. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
150. (c) Bloch, R. Chem. Rev. 1998, 98, 1407.
151. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
152. Taniyama, D.; Hasegawa, M.; Tomioka, K. Tetrahedron: Asymmetry 1999, 10, 221.
153. Taniyama, D.; Hasegawa, M.; Tomioka, K. Tetrahedron. Lett. 2000, 41, 5533.
154. Gluszynska, A.; Rozwadowska, M. D. Tetrahedron: Asymmetry 2000, 11, 2359.
155. Ponzo, V. L.; Kaufman, T. S. Tetrahedron Lett. 1995, 36, 9105.