Selected recent advances in the stereoselective synthesis of isoquinoline and β-carboline derivatives with the use of chiral auxiliaries of natural origin

Current Organic Synthesis

Volumn 2, Issue 3, 2005, Pages 301-331

  Czarnocki, Zbigniew ^a   Siwicka, Aleksandra ^a   Szawkało, Joanna ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

Alkaloids; Bischler Napieralski; Diastereomers; Enantiomers; Pictet Spengler; Stereochemistry

Indexed keywords

EID: 35948954875     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570179054368527     Document Type: Review

References (99)

1. Phillipson, J.D.; Roberts, M.F.; Zenk, M.H. (Eds.) The Chemistry and Biology of Isoquinoline Alkaloids, Springer-Verlag: New York, 1985.
2. Phillipson, J.D.; Zenk, M.H. (Eds.) Indole and Biogenetically Related Alkaloids, Academic Press: London, 1980.
3. Rahman, A.-U.; Basha, A. Biosynthesis of Indole Alkaloids, Clarendon Press: Oxford, 1983.
4. Zhu, H.J.; Zhao, B.T.; Zuo, G.Y.; Pittman, Jr.; Dai, W.M.; Hao, X.J. Tetrahedron: Asymmetry, 2001, 12, 2613.
5. Rozwadowska, M.D. Heterocycles, 1994, 39, 903.
6. Chrzanowska, M.; Rozwadowska, M.D. Chem. Rev., 2004, 104, 3341.
7. Scott, J.D.; Williams, R.M. Chem. Rev., 2002, 102, 1669.
8. Desmaäle, D.; Mekouar, K.; d'Angelo, J. J. Org. Chem., 1997, 62, 3890.
9. Whiting, A. Advanced Asymmetric Synthesis, Stephenson, G. R., Ed.; Blackie Academic & Professional: London, 1996.
10. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons., Inc.: New York, 1995.
11. Bols, M. Carbohydrate Building Blocks, Wiley: New York, 1996.
12. Collins, P.; Ferrier, R. Monosaccharides, Wiley: New York, 1995.
13. Soerens, D.; Sandrin, J.; Ungemach, F.; Mokry, P.; Wu, G.S.; Yamanaka, E.: Hutchins, L.; DiPierro, M.; Cook, J.M. J. Org. Chem., 1979, 44, 535.
14. Manini, P.; d'Ischia, M.; Lanzetta, R.: Parrilli, M.; Prota, G. Bioorg. Med. Chem., 1999, 7, 2525.
15. Martini, P.; d'Ischia, M.; Prota, G. Bioorg. Med Chem., 2001, 9, 923.
16. Czarnocki, Z.; MacLean, D.B.; Szarek, W.A. Can. J. Chem., 1986, 64, 2205.
17. Piper, I.M.; MacLean, D.B.; Kvarnström, I.; Szarek, W.A. Can. J. Chem., 1983, 61, 2721.
18. Manini, P.; d'Ischia, M.; Prota, G. J. Org. Chem., 2001, 66, 5048.
19. Mossine, V.V.; Glinsky, G.V.; Feather, M.S. Carbohydr. Res., 1994, 262, 257.
20. Kitajima, M.; Shirakawa, S.; Abdel-Moty, S.G.A.; Takayama, H.; Sakai, S.; Aimi, N.; Stöckigt, J. Chem. Pharm. Bull., 1996, 44, 2195
21. Tian, X.; Hudlicky, T.; Königsberger, K. J. Am. Chem. Soc., 1995, 117, 3643.
22. Keck, G.E.; McHardy, S.F.; Murry, J.A. J. Org. Chem., 1999, 64, 4465.
23. Czarnocki, Z.; Mieczkowski, J.B.; Ziólkowski, M. Tetrahedron: Asymmetry, 1996, 7, 2711.
24. Czarnocki, Z. J. Chem. Res. (S), 1992, 334.
25. Czarnocki, Z. J. Chem. Res. (S), 1992, 402,
26. Kaluza, Z.; Mostowicz, D. Tetrahedron: Asymmetry, 2003, 14, 225.
27. Greube, A.; Rommelspacher, H. J. Chromatogr. B, 2003, 784, 155.
28. Manabe, S.; Yuan, J.; Takahashi, T.; Urban, R.C. Exp. Eye Res., 1996, 63, 179.
29. Papavergou, E.; Herraiz, T. Food Res. Int., 2003, 36, 843.
30. Santos, L.S.; Fernandes, S.A.; Pilli, R.A.; Marsaioli, A.J. Tetrahedron: Asymmetry, 2003, 13, 2515.
31. Gremmen, C.; Wanner, M.J.; Koomen, G.-J. Tetrahedron Lett., 2001, 42, 8885.
32. Gremmen, C.; Willemse, B.; Warmer, M.J.; Koomen, G.-J. Org. Lett., 2000, 2, 1955.
33. Davis, F.A.; Andemichael, Y.W. Tetrahedron Letters, 1998, 39, 3099.
34. Ihara, M.; Yasui, K.; Taniguchi, N.; Fukumoto, K. J. Chem. Soc. Perkin Trans, 1, 1990, 1469.
35. Comins, D.L.; Badawi, M.M. Tetrahedron Letters, 1991, 32, 2995.
36. Tsuji, R.; Nakagawa, M.; Nishida, A. Tetrahedron: Asymmetry, 2003, 14, 177.
37. Pedrosa, R.; Andrés, C.; Iglesias, J. J. Org. Chem., 2001, 66, 243.
38. Corey, E.J.; Gin, D.Y. Tetrahedron Letters, 1996, 37, 7163.
39. Kawai, M.; Deng, Y.; Kimura, I.; Yamamura, H.; Araki, S.; Naoi, M. Tetrahedron: Asymmetry, 1996, 8, 1487.
40. Yamada, H.; Kawate, T.; Matsumizu, M.; Nishida, A.; Yamaguchi, K.; Nakagawa, M. J. Org. Chem., 1998, 63, 6348.
41. Czamocki, Z.; Ziólkowski, Z. Heterocycles, 1999, 51, 2871.
42. Oppolzer, W. Pure Appl. Chem., 1990, 43, 1969.
43. Kosior, M.; Malinowska, M.; Józwik, J.; Caille, J.C.; Jurczak, J. Tetrahedron: Asymmetry, 2003, 14, 239.
44. Gawley, R. E.; Zhang, P. J. Org. Chem., 1996, 61, 8103.
45. Popov, S.A.; Gatilov, Y.V.; Rybalova, T.V.; Tkachev, A.V. Tetrahedron: Asymmetry, 2003, 14, 233.
46. Gawronski, J.; Gawronska, K. Tartaric and Malic Acids in Synthesis, Wiley-Interscience: New York, 1999.
47. Dr̈nyei, G.; Szántay, Cs. Acta Chim. Acad. Sci. Hung., 1976, 89, 161.
48. Czarnocki, Z.; MacLean, D.B.; Szarek, W.A. Can. J. Chem., 1987, 65, 2356.
49. Ziólkowski, M.; Czarnocki, Z. Tetrahedron Letters, 2000, 41, 1963.
50. Jacques, J.; Collet, A.; Wilen, S.H. Enantiomers, Racemates and Resolution, Wiley and Sons: New York, 1981.
51. Suna, E. Synthesis, 2003, 2, 251.
52. Reiners, I.; Martens, J. Tetrahedron: Asymmetry, 1997, 8, 277.
53. Czarnocki, Z.; MacLean, D.B.; Szarek, W.A. Bull. Soc. Chim. Belg., 1986, 95, 749.
54. Hwang, D.J.; Kang, S.S.; Lee, J.Y.; Choi, J.H.; Park, H.; Lee, Y.S. Synth. Commun., 2002, 32, 2499.
55. Lee, J.Y.; Lee, Y.S.; Chung, B.Y.; Park, H. Tetrahedron, 1997, 53, 2449.
56. Ukaji, Y.; Yoshida, Y.; Inomata, K. Tetrahedron: Asymmetry, 2000, 11, 733.
57. Kang, J.; Kim, J.B.; Cho, K.H.; Cho, B.T. Tetrahedron: Asymmetry, 1997, 8, 657.
58. Arazny, Z.; Czarnocki, Z.; Wojtasiewicz, K.; Maurin, J.K. Tetrahedron: Asymmetry, 2000, 11, 2793.
59. Czarnocki, Z. J. Chem. Res. (S), 1992, 368.
60. Laumer, J.M.; Kim, D.D.; Beak, P. J. Org. Chem., 2002, 67, 6797.
61. Chrzanowska, M.; Sokolowska, J. Tetrahedron: Asymmetry, 2001, 12, 1435.
62. Alexakis, A.; Amiot, F. Tetrahedron: Asymmetry, 2002, 13, 2117.
63. Sharpless, K.B. J. Org. Chem., 1992, 57, 2768.
64. Wipf, P.; Hopkins, C.R. J. Org. Chem., 2001, 66, 3133.
65. Hirsenkorn, R. Tetrahedron Lett., 1990, 31, 7591.
66. Coppola, G.M.; Schuster, H.F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids, John Wiley & Sons: New York, 1987.
67. Sardina, F.J.; Rapoport, H. Chem. Rev., 1996, 96, 1825.
68. Vicario, J.L.; Badia, D.; Carrillo, L.; Etxebarria, J. Curr. Org. Chem., 2003, 7, 1775.
69. Garcia, E.; Arrasate, S.; Ardeo, A.; Lete, E.; Sotomayor, N. Tetrahedron Lett., 2001, 42, 1511.
70. Ardeo, A.; Garcia, E.; Arrasate, S.; Lete, E.; Sotomayor, N. Tetrahedron Lett., 2003, 44, 8445.
71. Bailey, P.D.; Hollinshead, S.P.; McLay, N.R.; Morgan, K.; Palmer, S.J.; Prince, S.N.; Reynolds, C.D.; Wood, S.D. J. Chem. Soc. Perkin Trans. I, 1993, 431.
72. Bailey, D.B.; Cochrane, P.J.; Lorenz, K.; Collier, I.D.; Pearson, P.J.; Rosair, G.M. Tetrahedron Lett., 2001, 42, 113.
73. Bailey, P.D.; Collier, I.D.; Hollinshead, S.P.; Moore, M.H.; Morgan, K.; Smith, D.I; Vernon, J.M. J. Chem. Soc. Perkin Trans. I, 1997, 1209.
74. Wang, H.; Ganesan, A. J. Org. Chem., 2000, 65, 4685
75. Yu, P.; Wang, T.; Cook, J.M. J. Org. Chem., 2000, 65, 3173.
76. Grigg, R.; MacLachan, W.S.; MacPherson, D.T.; Sridharan, V.; Suganthan, S.; Thornton-Pett, M.; Zhang, J. Tetrahedron, 2000, 56, 6585.
77. Horiguchi, Y.; Nakamura, M.; Saitoh, T.; Sano, T. Chem. Pharm. Bull., 2003, 51, 1368.
78. Dai, W.-M.; Zhu, H.J.; Hao, X.-J. Tetrahedron Lett., 1996, 37, 5971
79. Yamazaki, N.; Suzuki, H.; Aoyagi, S.; Kibayashi, Ch. Tetrahedron Lett., 1996, 37, 6161
80. Itoh, T.; Matsuya, Y.; Enomoto, Y.; Ohsawa, A. Tetrahedron, 2001, 57, 7277.
81. Itoh, T.; Yokoya, M.; Myiauchi, K.; Nagata, K.; Ohsawa, A. Org. Lett., 2003, 5, 4301.
82. Dickman, D.A.; Meyers, A.I. Tetrahedron Lett., 1986, 27, 1465.
83. see for example Cutter, P.S.; Miller, B.; Schore, N.E. Tetrahedron, 2002, 58, 1471.
84. Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J.M. J. Org. Chem., 2001, 66, 4525.
85. Ohba, M.; Kubo, H.; Ishibashi, H. Tetrahedron, 2000, 56, 7751.
86. Toda, J.; Matsumoto, S.; Saitoh, T.; Sano, T. Chem. Pharm. Bull., 2000, 48, 91.
87. Kawabata, T.; Öztürk, O.; Suzuki, H.; Fuji, K. Synthesis, 2003, 4, 505.
88. Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett, 1996, 85.
89. Daverio, P.; Zanda, M. Tetrahedron: Asymmetry, 2001, 12, 2225.
90. Yamada, K.; Takeda, M.; Ohtsuka, H.; Iwakuma, T. Chem. Pharm. Bull., 1983, 31, 70.
91. Hajipour, A.R.; Hantehzadeh, M. J. Org. Chem., 1999, 64, 8475.
92. Itoh, T.; Nagata, K.; Yokoya, M.; Myiazaki, M.; Kameoka, K.; Nakamura, S.; Ohsawa, A. Chem. Pharm. Bull., 2003, 51, 951.
93. Czarnocki, Z.; Mieczkowski, J.B. Pol. J. Chem., 1995, 69, 1447.
94. Zawadzka, A.; Leniewski, A.; Maurin, J.K.; Wojtasiewicz, K.; Czarnocki, Z. Org. Lett., 2001, 3, 997.
95. Siwicka, A.; Wojtasiewicz, K.; Leniewski, A.; Maurin, J.K.; Czarnocki, Z. Tetrahedron: Asymmetry, 2002, 13, 2295.
96. Zawadzka, A.; Leniewski, A.; Maurin, J.K.; Wojtasiewicz, K.; Siwicka, A.; Blachut, D.; Czarnocki, Z. Eur. J. Org. Chem., 2003, 13, 2443.
97. Krejcarek, G.E.; Dominy, B.W.; Lawton, R.G. Chem. Commun., 1968, 1450.
98. Speckamp, W.N.; Hiemstra, H. Tetrahedron, 1985, 41, 4367.
99. Castro, B.; Evin, G.; Selve, C.; Seyer, R. Tetrahedron Lett., 1975, 1219.