Electrophilic-induced cyclization reaction of hexahydroindolinone derivatives and its application toward the synthesis of (±)- erysotramidine

Journal of Organic Chemistry

Volumn 69, Issue 24, 2004, Pages 8209-8218

  Padwa, Albert ^a   Lee, Hyoung Ik ^a   Rashatasakhon, Paitoon ^a   Rose, Mickea ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; DERIVATIVES; ISOMERS; MIXTURES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AROMATIC SUBSTITUTION; CYCLIZATION; DIASTEREOMERS; PROTONATION;

KETONES;

1 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 1,4,5,6 TETRAHYDROINDOLINONE; ERYSOTRAMIDINE; ERYTHRINA ALKALOID; HEXAHYDROINDOLINONE DERIVATIVE; INDOLE DERIVATIVE; LACTAM DERIVATIVE; OCTAHYDROPYRIDO[2,1 I]INDOLINONE DERIVATIVE; PYRROLO[3,2,1 IJ]QUINOLINONE DERIVATIVE; QUINOLINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDOLES; LACTAMS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 9344243559     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048647f     Document Type: Article

References (120)

1. (a) Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press, Inc.: New York, 1987; Vol. 30, pp 251-377.
2. (b) Lewis, J. R. Nat. Prod. Rep. 1994, 11, 329.
3. Jeffs, P. W. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 19, pp 1-80.
4. (a) Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 199-384.
5. (b) Saxton, J. E. Nat. Prod. Rep. 1993, 10, 349-395.
6. (a) Boekelheide, V. Alkaloids 1960, 7, 201.
7. (b) Hill, R. K. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 483.
8. Dyke, S. F.; Quessy, S. N. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 18, pp 1-98.
9. (a) Massiot, G.; Delaude, C. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, CA, 1988; Vol. 34, pp 211-329.
10. (b) Aimi, N.; Sakai, S.; Ban, Y. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, CA, 1989; Vol. 36, pp 1-68.
11. (c) Bosch, J.; Bonjoch, J.; Amat, M. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, CA, 1996; Vol. 48, pp 75-189.
12. For some leading references, see: (a) Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671.
13. (b) Grothjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579.
14. (c) Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783.
15. (d) Backvall, J. E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988.
16. (e) Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536.
17. (f) Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
18. (a) Kuehne, M. E.; Matsko, T. H.; Bohnert, J. C.; Motyka, L.; Oliver-Smith, D. J. Org. Chem. 1981, 46, 2002.
19. (b) Kuehne, M. E.; Earley, W. G. Tetrahedron 1983, 39, 3707.
20. (c) Kuehne, M. E.; Brook, C. S.; Xu, F.; Parsons, R. Pure Appl. Chem. 1994, 66, 2095.
21. (d) Nkiliza, J.; Vercauteren, J. Tetrahedron Lett. 1991, 32, 1787.
22. (e) Rawal, V. H.; Michoud, C.; Monestel, R. F. J. Am. Chem. Soc. 1993, 46, 3030.
23. (a) Overman, L. E.; Sugai, S. Helv. Chim. Acta 1985, 68, 745.
24. (b) Overman, L. E.; Robertson, G.; Robichaud, A. J. J. Org. Chem. 1989, 54, 1236.
25. (c) Overman, L. E.; Sworin, M.; Burk, R. M. J. Org. Chem. 1983, 48, 2685.
26. (a) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35.
27. (b) Gallagher, T.; Magnus, P.; Huffman, J. C. J. Am. Chem. Soc. 1983, 105, 4750.
28. (c) Desmaële, D.; d'Angelo, J. J. Org. Chem. 1994, 59, 2292.
29. (a) Kraus, G. A.; Thomas, P. J.; Bougie, D.; Chen, L. J. Org. Chem. 1990, 55, 1624.
30. (b) Sole, D.; Bonjoch, J. Tetrahedron Lett. 1991, 32, 5183.
31. (c) Bonjoch, J.; Sole, D.; Bosch, J.; J. Am. Chem. Soc. 1993, 115, 2064.
32. (d) Schultz, A. G.; Guzzo, P. R.; Nowak, D. M. J. Org. Chem. 1995, 60, 8044.
33. (e) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1993, 115, 7904.
34. (f) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210.
35. (a) Padwa, A.; Price, A. T. J. Org. Chem. 1995, 60, 6258.
36. (b) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662.
37. (a) Rigby, J. H.; Qabar, M.; Ahmed, G.; Hughes, R. C. Tetrahedron 1993, 49, 10219.
38. (b) Rigby, J. H.; Laurent, S.; Cavezza, A.; Heeg, M. J. J. Org. Chem. 1998, 63, 5587.
39. (c) Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 7834.
40. (d) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569.
41. (e) Rigby, J. H.; Qabar, M. H. J. Org. Chem. 1993, 58, 4473.
42. (a) Mori, M.; Kuroda, S.; Zhang, C.; Sato, Y. J. Org. Chem. 1997, 62, 3263.
43. (b) Uesaka, N.; Saitoh, F.; Mori, M.; Shibasaki, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 5633.
44. (c) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1992, 443.
45. Chawla, A. S.; Kapoor, V. K. In The Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: 1995; Vol. 9, pp 86-153.
46. Tsuda, Y.; Sano, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1996; Vol. 48, pp 249-337.
47. Kawasaki, T.; Onoda, N.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 2001, 42, 8003.
48. (a) Belleau, B. J. Am. Chem. Soc. 1953, 75, 5765.
49. (b) Mondon, A.; Hansen, K. F. Tetrahedron Lett. 1960, 5.
50. (c) Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
51. (d) Tsuda, Y.; Hosoi, S.; Ishida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204.
52. (e) Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron Lett. 1998, 39, 8995.
53. (f) Rigby, J. H.; Deur, C.; Heeg, M. J. Tetrahedron Lett. 1999, 40, 6887.
54. (g) Parsons, A. F.; Williams, D. A. Tetrahedron 2000, 56, 7217.
55. (h) Toyao, A.; Chikaoka, S.; Takeda, Y.; Tamura, O.; Muraoka, O.; Tanabe, G.; Ishibashi, H. Tetrahedron Lett. 2001, 42, 1729.
56. (i) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135.
57. (j) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464.
58. (k) Guerrero, M. A.; Cruz-Almanza, R.; Miranda, L. D. Tetrahedron 2003, 59, 4953.
59. (a) Toda, J.; Niimura, Y.; Takeda, K.; Sano, T.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 906.
60. (b) Jousse, C.; Demaële, D.; Eur. J. Org. Chem. 1999, 909.
61. Wasserman, H. H.; Amici, R. M. J. Org. Chem. 1989, 54, 5843.
62. (a) Sano, T.; Toda, J.; Kashiwaba, N.; Ohshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479.
63. (b) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Heterocycles 1992, 33, 497.
64. (a) Danishefsky, S. J.; Panek, J. S. J. Am. Chem.. Soc. 1987, 109, 917.
65. (b) Ahmed-Schofield, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478.
66. (c) Irie, H.; Shibata, K.; Matsuno, K.; Zhang, Y. Heterocycles 1989, 29, 1033.
67. (d) Kawasaki, T.; Onoda, N.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 2001, 42, 8003.
68. (a) Gervay, J. E.; McCapra, F.; Money, T.; Sharma, G. M. J. Chem. Soc., Chem. Commun. 1966, 142.
69. (b) Tanaka, H.; Shibata, M.; Ito, K. Chem. Pharm. Bull. 1984, 32, 1578.
70. (c) Chou, C. T.; Swenton, J. S. J. Am. Chem. Soc. 1987, 109, 6898.
71. (a) Mondon, A.; Ehrhardt, M. Tetrahedron Lett. 1966, 2557.
72. (b) Haruna, M.; Ito, K. J. Chem. Soc., Chem. Commun. 1976, 345.
73. (c) Ishibashi, H.; Sato, K.; Ikeda, M.; Maeda, H.; Akai, S.; Tamura, Y. J. Chem. Soc., Perkin Trans. 1 1985, 605.
74. (d) Westling, M.; Smith, R.; Livinghouse, T. J. Org. Chem. 1986, 51, 1159.
75. (e) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312.
76. (a) Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888.
77. (b) Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144.
78. (c) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235.
79. For reviews of the chemistry of N-acyliminium ion cyclizations, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
80. (b) Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Academic Press: New York, 1988; Vol. 32, pp 271-339.
81. (c) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047-1082.
82. (d) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
83. (e) Maryanoff, B. E.; Zhang, H. C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431.
84. de Koning, H.; Speckamp, W. N. In Stereoselective Synthesis [Houben-Weyl]; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Workbench ed E21, Vol. 3, pp 1952-2010.
85. For some recent examples, see: (a) Luker, T.; Koot, W. J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1988, 53, 220.
86. (b) Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T.; McClure, M. S. J. Org. Chem. 1998, 63, 6778.
87. (c) Lee, Y. S.; Lee, J. Y.; Kim, D. W.; Park, H. Tetrahedron 1999, 55, 4631.
88. (d) Lee, Y. S.; Cho, D. J.; Kim, S. N.; Choi, J. H.; Park, H. J. Org. Chem. 1999, 64, 9727.
89. (e) Ducrot, P.; Thal, C. Tetrahedron Lett. 1999, 40, 9037.
90. (f) Consonni, A.; Danieli, B.; Lesma, G.; Passarella, D.; Piacenti, P.; Silvani, A. Eur. J. Org. Chem. 2001, 1373.
91. (g) Padwa, A. Pure Appl. Chem. 2003, 75, 47.
92. For some representative examples, see: (a) Speckamp, W. N. Rec. Trav. Chim. Pays-Bas 1981, 345.
93. (b) Maryanoff, B. E.; McComsey, D. F.; Duhl-Emswiler, B. A. J. Org. Chem. 1983, 48, 5062.
94. (c) Kano, S.; Yuasa, Y.; Yokomatsu, T.; Shibuya, S. J. Org. Chem. 1983, 48, 3835.
95. (d) Maryanoff, B. E.; McComsey, D. F.; Almond, H. R., Jr.; Mutter, M. S. J. Org. Chem. 1986, 51, 1341.
96. (e) Ent, H.; Koning, H.; Speckamp, W. N. Heterocycles 1988, 27, 237.
97. (f) Bahajaj, A. A.; Vernon, J. M.; Wilson, G. D. J. Chem. Soc., Perkin Trans. 1 2001, 1446.
98. (g) Katritzky, A. R.; Mehta, S.; He, H. Y. J. Org. Chem. 2001, 66, 148.
99. Lee, H. I.; Cassidy, M. P.; Rashatasakhon, P.; Padwa, A. Org. Lett. 2003, 5, 5067.
100. (a) Ragan, J. A.; Claffey, M. C. Heterocycles 1995, 41, 57.
101. (b) Ennis, M. D.; Hoffman, R. L.; Ghazal, N. B.; Old, D. W.; Mooney, P. A. J. Org. Chem. 1996, 61, 5813.
102. (a) Wilkens, H. J.; Traxler, F. Helv. Chim. Acta 1975, 58, 1512.
103. (b) Mondon, A.; Hansen, K. F.; Boehme, K.; Faro, H. P.; Nestler, H. J.; Vilhuber, H. G.; Böttcher, K. Chem. Ber. 1970, 103, 615.
104. (c) Mondon, A.; Nestler, H. J. Chem. Ber. 1979, 112, 1329.
105. (d) Dean, R. T.; Rapoport, H. A. J. Org. Chem. 1978, 43, 4183.
106. The β-erythroidine skeleton has been prepared by an oxidative degradation of the aromatic ring (ring A) in erythrinans as the key step; see: Isobe, K.; Mohri, K.; Itoh, Y.; Toyokawa, Y.; Takeda, N.; Taga, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1992, 40, 2632.
107. Johnson, W. S.; Ward, C. E.; Boots, S. G.; Gravestock, M. B.; Markezich, R. L.; McCarry, B. E.; Okorie, D. A.; Parry, R. J. Am. Chem.. Soc. 1981, 103, 88.
108. Schoemaker, H. E.; Boer-Terpstra, T.; Dijkink, J.; Speckamp, W. N. Tetrahedron 1980, 36, 143. Boer-Terpstra, T.; Dijkink, J.; Shoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1977, 939.
109. Schoemaker, H. E.; Boer-Terpstra, T.; Dijkink, J.; Speckamp, W. N. Tetrahedron 1980, 36, 143. Boer-Terpstra, T.; Dijkink, J.; Shoemaker, H. E.; Speckamp, W. N. Tetrahedron Lett. 1977, 939.
110. Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 1988, 110, 612. Overman, L. E.; Sharp, M. J. Tetrahedron Lett. 1988, 29, 901.
111. Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 1988, 110, 612. Overman, L. E.; Sharp, M. J. Tetrahedron Lett. 1988, 29, 901.
112. This suggestion was made by on of the reviewers.
113. Lee, Y. S.; Lee, J. Y.; Kim, D. W.; Park, H. Tetrahedron 1999, 55, 4631.
114. (a) Ito, K.; Suzuki, F.; Haruna, M. J. Chem. Soc., Chem. Commun. 1978, 733.
115. (b) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
116. (c) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505.
117. Asselin, A. A.; Humber, L. G.; Dobson, T. A.; Komlossy, J.; Martel, R. R. J. Med. Chem. 1976, 19, 787.
118. Hexahydroindolinone 33 was prepared by the selective bromination of 28 followed by a palladium-catalyzed cross-coupling reaction with vinyl tributyltin and a subsequent catalytic hydrogenation of the vinyl group. Details of the procedure are described in the Supporting Information.
119. Coates, R. M.; Pigott, H. D.; Ollinger, J. Tetrahedron Lett. 1974, 15, 3955.
120. Toda, J.; Niimura, Y.; Takeda, K.; Sano, T.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 906.