Synthesis of isoindolobenzazepine alkaloids based on radical reactions or Pd(0)-catalyzed reactions (Journal of Organic Chemistry (2009) 74, (5486) DOI: 10.1021/jo900311g);Synthesis of isoindolobenzazepine alkaloids based on radical reactions or Pd(0)-catalyzed reactions

Journal of Organic Chemistry

Volumn 74, Issue 15, 2009, Pages 5486-5495

  Onozaki, Yu ^a   Kurono, Nobuhito ^a,b   Senboku, Hisanori ^a,b   Tokuda, Masao ^a   Orito, Kazuhiko ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b Division of Chemical Process Engineering

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOIDS; CARBONYLATION; CATALYSIS; METABOLITES; REACTION KINETICS;

A-RINGS; CATALYZED REACTIONS; CHEMICAL EQUATIONS; CYANO GROUPS; FORMAL SYNTHESIS; RADICAL REACTIONS;

CYCLIZATION;

1 CYANO 2 (2 IODO 3,4 DIMETHOXYPHENYL) 3 METHYL 7,8 (METHYLENEDIOXY) 1,2,4,5 TETRAHYDRO 3H 3 BENZAZEPINE; 1 CYANO 2 (2 IODO 3,4 DIMETHOXYPHENYL) 7,8 (METHYLENEDIOXY) 1,2,4,5 TETRAHYDRO 3H 3 BENZAZEPINE; 1 CYANO 2 (3,4 DIMETHOXYPHENYL) 7,8 (METHYLENEDIOXY) 1,2,3,4 TETRAHYDRO 3H 3 BENZAZEPINE; 2 (2 BROMO 3,4 DIMETHOXYPHENYL) 1 CYANO 3 METHYL 7,8 (METHYLENEDIOXY) 1,2,4,5 TETRAHYDRO 3H 3 BENZAZEPINE; 2 (2 BROMO 3,4 DIMETHOXYPHENYL) 1 CYANO 7,8 (METHYLENEDIOXY) 1,2,4,5 TETRAHYDRO 3H 3 BENZAZEPINE; 2 (2 BROMO 4,5 DIMETHOXYPHENYL) 1 CYANO 7,8 (METHYLENEDIOXY) 1,2,4,5 TETRAHYDRO 3H 3 BENZAZEPINE; 2 (2 CYANO 3,4 DIMETHOXYPHENYL) 3 METHYL 7,8 (METHYLENEDIOXY) 1,2,4,5 TETRAHYDRO 3H 3 BENZAZEPINE; 2 (2 CYANO 3,4 DIMETHOXYPHENYL) 7,8 (METHYLENEDIOXY) 1,2,4,5 TETRAHYDRO 3H 3 BENZAZEPINE; 2 (2 CYANO 3,4 DIMETHOXYPHENYL) 7,8 (METHYLENEDIOXY) 4,5 DIHYDRO 3H 3 BENZAZEPINE; 2 (2 CYANO 4,5 DIMETHOXYPHENYL) 7,8 (METHYLENEDIOXY) 4,5 DIHYDRO 3H 3 BENZAZEPINE; 3 (6 BROMO 2,3 DIMETHOXYBENZOYL) 7,8 (METHYLENEDIOXY) 1,2 DIHYDRO 3H 3 BENZAZEPINE; ALKALOID; BENZAZEPINE DERIVATIVE; CHELENINE; ISOINDOLOBENZAZEPINE; LENNOXAMINE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CONTROLLED STUDY; CYCLIZATION; RADICAL REACTION; SYNTHESIS;

ALKALOIDS; BENZAZEPINES; CATALYSIS; CYCLIZATION; FREE RADICALS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 68049106278     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901373g     Document Type: Erratum

References (109)

1. (a) Shamma, M. The Alkaloids; Academic Press: New York, 1972; p 408.
2. (b) Shamma, M.; Moniot, J. L. Isoquinoline Alkaloids Research 1972-1977; Plenum Press: New York, 1978; p 300.
3. (c) Fajardo, V.; Elango, V.; Cassels, B. K.; Shamma, M. Tetrahedron Lett. 1982, 23, 39-42.
4. (d) Valencia, E.; Weiss, I.; Firdous, S.; Freyer, A. J.; Shamma, M.; Urzua, A.; Fajardo, V. Tetrahedron 1984, 40, 3957-3962.
5. (e) Valencia, E.; Freyer, A.; Shamma, M.; Fajardo, V. Tetrahedron Lett. 1984, 25, 599-602.
6. For a-bond, see: (a) Bernhard, H. O.; Snieckus, V. Tetrahedron Lett. 1971, 51, 4867-4870.
7. (b) Ishibashi, H.; Kawanami, H.; Iriyama, H.; Ikeda, M. Tetrahedron Lett. 1995, 36, 6733-6734.
8. (c) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780-2782.
9. (d) Ishibashi, H.; Kawanami, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 817-821.
10. (e) Koseki, Y.; Kusano, S.; Sakata, H.; Nagasaka, T. Tetrahedron Lett. 1999, 40, 2169-2172.
11. (f) Kim, G.; Kim, J. H.; Kim, W.-j.; Kim, Y. Tetrahedron Lett. 2003, 44, 8207-8209.
12. For b-bond, see: (a) Ruchirawat, S.; Lertwanawatana, W.; Thianpatanagul, S.; Cashaw, J. L.; Davis, V. E. Tetrahedron Lett. 1984, 25, 3485-3488.
13. (b) Mazzocchi, P. H.; King, C. R.; Ammon, H. L. Tetrahedron Lett. 1987, 28, 2473-2476.
14. (c) Kessar, S. V.; Singh, T.; Vohra, R. Tetrahedron Lett. 1987, 28, 5323-5326.
15. (d) Fang, F. G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 30, 2747-2750.
16. (e) Daich, A.; Marchalin, S.; Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 9187-9190.
17. (f) Kessar, S. V.; Singh, T.; Vohra, R. Indian J. Chem. 1991, 30B, 999-1005.
18. (g) Ruchirawat, S.; Sahakitpichan, P. Tetrahedron Lett. 2000, 41, 8007-8010.
19. (h) Padwa, A.; Beall, L. S.; Eidell, C. K.; Worsenvroft, K. J. J. Org. Chem. 2001, 66, 2414-2421.
20. (i) Yoda, H.; Nakamura, A.; Koketsu, T.; Takabe, K. Tetrahedron Lett. 2002, 43, 4667-4669.
21. (j) Sahakitpichan, P.; Ruchirawat, S. Tetrahedron 2004, 60, 4169-4172.
22. (k) Comins, D. L.; Schilling, S.; Zhang, Y. Org. Lett. 2005, 7, 95-98.
23. For c-bond, see: (a) Moniot, J. L.; Hindenlang, D. M.; Shamma, M. J. Org. Chem. 1979, 44, 4347-4351.
24. (b) Dorn, C. R.; Koszyk, F. J.; Lenz, G. R. J. Org. Chem. 1984, 49, 2642-2644.
25. (c) Chiefari, J.; Janowski, W.; Prager, R. Tetrahedron Lett. 1986, 27, 6119-6122.
26. (d) Rodríguez, G.; Castedo, L.; Domínguez, D.; Saá, C. Tetrahedron Lett. 1998, 39, 6551-6554.
27. (e) Kessar, S. V.; Singh, T.; Vohra, R. Indian J. Chem. 1991, 30B, 299-231.
28. (f) Reference 2c.
29. For d-bond, see: (a) Barili, P. L.; Fiashi, R.; Napolitano, E.; Pistelli, L.; Scartoni, V.; Marsili, A. J. Chem. Soc., Perkin Trans. I 1981, 1654-1658.
30. (b) Koseki, Y.; Nagasaka, T. Chem. Pharm. Bull. 1995, 43, 1604-1606.
31. (c) Napolitano, E.; Spinelli, G.; Fiaschi, R.; Marsili, A. J. Chem. Soc., Perkin Trans. 1 1986, 785-787.
32. (d) Koseki, Y.; Kusano, S.; Sakata, H.; Sato, H.; Nagasaka, T. Tetrahedron Lett. 1999, 40, 2169-2172.
33. (e) Couture, A.; Deniau, E.; Grandclaudon, P.; Hoarau, C. Tetrahedron 2000, 56, 1491-1499.
34. (f) Koseki, Y.; Katsura, S.; Kusano, S.; Sakata, H.; Sato, H.; Monzene, Y.; Nagasaka, T. Heterocycles 2003, 59, 527-540.
35. (g) Couty, S.; Meyer, C.; Cossy, J. Tetrahedron Lett. 2006, 47, 767-769.
36. (h) Couty, S.; Liegault, B.; Meyer, C.; Cossy, J. Tetrahedron 2006, 62, 3882-3895.
37. For e-bond, see: (a) Yasuda, S.; Sugimoto, Y.; Mukai, C.; Hanaoka, M. Heterocycles 1990, 30, 335-337.
38. (b) Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3923-2925.
39. (c) Taniguchi, T.; Iwasaki, K.; Uchiyama, M.; Tamura, O.; Ishibashi, H. Org. Lett. 2005, 7, 4389-4390.
40. (d) Honda, T.; Sakamaki, Y. Tetrahedron Lett. 2005, 46, 6823-6825.
41. For f-bond, see. (a) Teitel, S.; Klötzer, W.; Borgese, J.; Brossi, A. Can. J. Chem. 1972, 50, 2022-2024.
42. (b) Moody, C. J.; Warrellow, G. J. Tetrahedron Lett. 1987, 28, 6089-6092.
43. Moody, C. J.; Warrellow, G. J. J. Chem. Soc., Perkin Trans. 1 1990, 2929-2936
44. For reviews on the Pd-catalyzed Heck reaction, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
45. (b) Whitcombe, N J.; Hii, K. K. (M.); Gibson, S. E. Tetrahedron 2001, 57, 7440-7476.
46. (c) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
47. (d) Dyker, G. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New Yori, 2002; Vol. 1, pp 1255-1282.
48. (e) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2963.
49. (f) For recent references, see:Berthiol, F.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2003, 44, 1221-1225.
50. (a) Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684-1687.
51. (b) Mori, M.; Chiba, K.; Inotsume, N.; Ban, M. Heterocycles 1979, 12, 921-924.
52. (a) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation, Direct Synthesis of Carbonyl Compound; Plenum Press: New York, 1991; pp 191-204.
53. (b) Tsuji, J. Palladium Reagents and Catalysts, Innovation in Organic Synthesis; John Willey & Sons: Chichester, U.K., 1995; pp 188-209.
54. (c) Tkatchenko, I. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, UK, 1982; Vol. 8, pp 101-223.
55. For reviews on aryl radical cyclization, see: (a) Ikeda, M.; Sato, T.; Ishibashi, H. Rev. Heteroatom Chem. 1998, 18, 169-198.
56. (b) Banik, B. K. Curr. Org. Chem. 1999, 3, 469-496.
57. (c) Murphy, J. A. Pure Appl. Chem. 2000, 72, 1327-1334.
58. (d) Ishibasi, H. Chem. Rec. 2006, 6, 23-31.
59. (e) For recent references, see: Zhou, A.; Niogu, M. N.; Pittman, C. U. Jr. Tetrahedron 2006, 62, 4093-4102.
60. (a) Pecherer, B.; Sunbury, R. C.; Brossi, A. J. Heterocycl. Chem. 1972, 9, 609-616.
61. (b) Orito, K.; Kaga, H.; Itoh, M.; de Silva, S. O.; Manske, R. H.; Rodrigo, R. J. Heterocycl. Chem. 1980, 417-423.
62. For formation of 1-oxoisoindolines by a 1,5-hydrogen atom transfer by aryl radicals generated from o-halobenzamides followed by cyclization of the resulting α-amidoyl radical, see: (a) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898.
63. (b) Curran, D. P.; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1393.
64. (c) Beckwith, A. L. J.; Storey, J. M. D. J. Chem. Soc., Chem. Commun. 1995, 977-978.
65. (d) Ikeda, M.; Kugo, Y.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1996, 1819-1824.
66. Dallacker, F.; Bernabei, D.; Katzke, R.; Benders, P.-H. Chem. Ber. 1971, 104, 2517-2525.
67. (a) Ikeda, M.; El Bialy, S. A. A.; Yakura, T. Heterocycles 1999, 51, 1957-1970.
68. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1990, 46, 4003-4018.
69. (c) Comins, D. L.; Joseph, S. P.; Zhang, Y. Tetrahedron Lett. 1996, 37, 793-796.
70. (d) García, A.; Rodríguez, D.; Castedo, L.; Saá, C.; Domíngues, D. Tetrahedron Lett. 2001, 42, 1903-1905.
71. (e) Lauthens, M.; Fang, Y.-Q. Org. Lett. 2003, 5, 3679-3682.
72. (f) Ackermann, A.; Kaspar, L. T.; Gschrei, C. J. Chem. Commun. 2004, 2824-2825.
73. (g) Wada, Y.; Nishida, N.; Kurono, N.; Ohkuma, T.; Orito, K. Eur. J. Org. Chem. 2007, 4320-4327.
74. (a) Plevyak, J. E.; Dickerson, J. K.; Heck, R. F. J. Org. Chem. 1979, 44, 4078-4080.
75. (b) Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1989, 54, 1502-1505.
76. (a) Larock, R. C.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629-6632.
77. (b) Amatore, C.; Azzabi, M.; Jutand, A. W. J. Am. Chem. Soc. 1991, 113, 8375-8384.
78. (c) Jeffery, T. Tetrahedron 1996, 52, 10113-10130.
79. For Heck vs. radical cyclizations, see: (a) Sundberg, R. J.; Cherney, R. J. J. Org. Chem. 1990, 55, 6028-6037.
80. (b) Ishibashi, H.; Ito, K.; Tabuchi, M.; Ikeda, M. Heterocycles 1991, 32, 1279-1282.
81. (c) Kraus, G. A.; Kim, H. Synth. Commun. 1993, 23, 55-64.
82. (d) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662.
83. (e) Cossy, J.; Peglion, J.-L.; Dpardo, D. G. Tetrahedron Lett. 1998, 39, 2965-2968.
84. (f) Frey, D. A.; Duan, C.; Ghiviriga, I.; Hudlicky, T. Collect. Czech. Chem. Commun. 2000, 65, 561-569.
85. (g) Denieul, M.-P.; Laursen, B.; Hhhazell, R.; Skrydstrup, T. J. Org. Chem. 2000, 65, 6052-6060.
86. (h) Kundig, P.; Ratni, H.; Crousse, B.; Bernardinelli, G. J. Org. Chem. 2001, 66, 1852-1860.
87. Orito, K.; Suginome, H. Heterocycles 1989, 29, 403-409.
88. Sinhababu, A. K.; Borchardt, R. T. J. Org. Chem. 1983, 48, 2356-2360.
89. Suzuki, H.; Kondo, A.; Ogawa, T. Chem. Lett. 1995, 411-412.
90. Gribble, G. W.; Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137-4140.
91. (a) Donetti, A.; Boniardi, O.; Ezhaya, A. Synthesis 1980, 1009-1011.
92. (b) Hatzigrigoriou, E.; Wartski, L. Bull. Soc. Chem. Fr. 1983, II-313-II-316.
93. (a) Murray, R. W.; Rajadhyaksha, S. N.; Mohan, L. J. Org. Chem. 1989, 54, 5783-5788.
94. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201.
95. Schröder, M. Chem. Rev. 1980, 80, 187-213.
96. Miyashita, M.; Suzuki, T.; Yoshikoshi, A. Chem. Lett. 1987, 285-288.
97. Ogino, T.; Mochizuki, K. Chem. Lett. 1979, 443-445.
98. For radical 1,4-migration of a cyano group, see: (a) Kalvoda, J. Helv. Chim. Acta, 1968, 51, 267-277;
99. Kalvoda, J. Chem. Commun. 1970, 1002-1003.
100. (b) Watt, D. S. J. Am. Chem. Soc. 1976, 98, 271-273.
101. (c) Roberts, B. P.; Winter, J. N. J. Chem. Soc., Perkin II 1979, 1353-1361.
102. (d) Beckwith, A. L. J.; O'Shea, D. M.; Gerba, S.; Westwood, S. W. J. Chem. Soc., Chem. Commun. 1987, 666-667.
103. (e) Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565-2575.
104. (f) Curran, D. P.; Seong, C. M. J. Am. Chem. Soc. 1990, 112, 9401-9403.
105. (g) Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2175-2190.
106. (h) Callier, A.-C.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 1994, 35, 6109-6112.
107. (i) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peeglion, J. L. Synthesis 1995, 1368-1370.
108. (j) Rychnovsky, S. D.; Swenson, S. S. Tetrahedron 1997, 53, 16489-16502.
109. (k) Crich, D.; Bowers, A. A. J. Org. Chem. 2006, 71, 3452-3463.