Development of samarium diiodide-promoted reductive carbon-nitrogen bond cleavage reaction of α-amino carbonyl compounds: Application to the synthesis of biologically active alkaloids

Heterocycles

Volumn 83, Issue 1, 2011, Pages 1-46

  Honda, Toshio ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952011062     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/REV-10-684     Document Type: Article

References (232)

1. P. Girard, J. L. Namy, and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693.
2. 2-mediated reaction, see: (a) J. Inanaga, J. Org. Synth. Chem., 1989, 47, 200;
3. (b) J. A. Soderquist, Aldrichim. Acta, 1991, 24, 15;
4. (c) D. P. Curran, T. L. Fevig, C. P. Jasperse, and M. J. Totleben, Synlett, 1992, 943;
5. (d) G. A. Molander, Chem. Rev., 1992, 92, 29;
6. (e) G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307;
7. (f) T. Skrydstrup, Angew. Chem., Int. Ed. Engl., 1997, 36, 345;
8. (g) G. A. Molander and C. R. Harris, Tetrahedron, 1998, 54, 3321;
9. (h) R. Nomura and T. Endo, Chem. Eur. J., 1998, 4, 1605;
10. (i) A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745;
11. (j) P. G. Steel, J. Chem. Soc., Perkin Trans. 1, 2001, 2727;
12. (k) S. Agarwal and A. Greiner, J. Chem. Soc., Perkin Trans. 1, 2002, 2033;
13. (l) H. B. Kagan, Tetrahedron, 2003, 59, 10351;
14. (m) M. Berndt, S. Gross, A. Hölemann, and H.-U. Reissig, Synlett, 2004, 422;
15. (n) D. J. Edmonds, D. Johnston, and D. J. Procter, Chem. Rev., 2004, 104, 3371;
16. (o) D. Y. Jung and Y. H. Kim, Synlett, 2005, 3019;
17. (p) K. Gopalaiah and H. B. Kagan, New J. Chem., 2008, 32, 607;
18. (q) I. M. Rudkin, L. C. Miller, and D. J. Procter, Organomet. Chem., 2008, 34, 19;
19. (r) K. C. Nicolaou, S. P. Ellery, and J. S. Chen, Angew. Chem. Int. Ed., 2009, 48, 7140;
20. (s) D. J. Procter, R. A. Flowers, II, and T. Skrydstrup, Organic Synthesis Using Samarium Diiodide: A Practical Guide; Royal Society of Chemistry Publishing: UK, 2010; p. 204.
21. (a) T. Honda, S. Yamane, K. Naito, and Y. Suzuki, Heterocycles, 1994, 37, 515;
22. (b) T. Honda, F. Ishikawa, and S. Yamane, J. Chem. Soc., Chem. Commun., 1994, 499;
23. (c) T. Honda, S. Yamane, K. Naito, and Y. Suzuki, Heterocycles, 1995, 40, 301;
24. (d) T. Honda, F. Ishikawa, and S. Yamane, J. Chem. Soc., Perkin Trans. 1, 1996, 1125;
25. (e) T. Honda, S. Yamane, F. Ishikawa, and M. Katoh, Tetrahedron, 1996, 37, 12177;
26. (f) T. Honda, M. Katoh, and S. Yamane, J. Chem. Soc., Perkin Trans. 1, 1996, 2219;
27. (g) T. Honda and M. Katoh, Chem. Commun., 1997, 369.
28. T. Honda and F. Ishikawa, Chem. Commun., 1999, 1065.
29. (a) G. A. Molander and P. J. Stengel, J. Org. Chem., 1995, 60, 6660;
30. (b) G. A. Molander and P. J. Sangel, Tetrahedron, 1997, 53, 8887;
31. (c) N. H. Kawahara and M. Goodman, Tetrahedron Lett., 1999, 40, 2271.
32. (a) J. M. Aurrecoechea and A. Fernandez-Acebes, Tetrahedron Lett., 1993, 34, 549;
33. (b) J. M. Aurrecoechea and A. Fernandez-Acebes, Synlett, 1996, 39;
34. (c) A. R. Katritzky, M. Qi, D. Feng, and D. A. Nichols, J. Org. Chem., 1997, 62, 4121.
35. H.-Y. Kang, A. N. Pae, Y. S. Cho, H. Y. Koh, and B. Y. Chung, Chem. Commun., 1997, 821.
36. The starting phenylalanine derivatives were prepared from the methyl ester by the known procedures;
37. N-methyl derivative: M. C. Allen, W. Fuhrer, B. Tuck, R. Wade, and J. M. Wood, J. Med. Chem., 1989, 32, 1652;
38. N,N-dimethyl derivative: T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki, and M. Kumada, J. Org. Chem., 1983, 48, 2195;
39. N-benzyl derivative: F. Effenberger, U. Burkard, and J. Willfahrt, Liebigs Ann. Chem., 1986, 314;
40. N,N-dibenzyl derivative: B. D. Gray and P. W. Jeffs, J. Chem. Soc., Chem. Commun., 1987, 1329;
41. N-acetyl derivative: M. J. Burk, J. E. Feaster, E.H. Harlow, and L. Richard, Tetrahedron: Asymmetry, 1991, 2, 569;
42. N-Boc derivative: M. Sakaitani and Y. Ohfune, J. Org. Chem., 1990, 55, 870.
43. N-Benzylproline methyl ester was prepared from methyl prolinate: V. Ferey, P. Vedrenne, L. Toupet, T. L. Gall, and C. Mioskowski, J. Org. Chem., 1996, 61, 7244;
44. isopropyl 4-tert-butyldimethylsiloxyprolinate was prepared by silylation of the corresponding ester, which on N-benzylation with BnBr and NaH gave the N-benzyl derivative.
45. 22O.
46. 2O; the N-Boc derivative was prepared according to the known procedure: S. Aoyagi, T.-C. Wang, and C. Kibayashi, J. Am. Chem. Soc., 1993, 115, 11393.
47. (a) J. Inanaga, M. Ishikawa, and M. Yamaguchi, Chem. Lett., 1987, 1485;
48. (b) E. Hasegawa and D. P. Curran, Tetrahedron Lett., 1993, 34, 1717;
49. (c) F. Machrouhi, B. Hamann, J.-L. Namy, and H. B. Kagan, Synlett, 1996, 633;
50. (d) M. Shabangi and R. A. Flowers, II, Tetrahedron Lett., 1997, 38, 1137;
51. (e) M. Shabangi, J. M. Sealy, J. R. Fuchs, and R. A. Flowers, II, Tetrahedron Lett., 1998, 39, 4429.
52. For a recent review of the coccinellied alkaloids, see: A. G. King and J. Meinwald, Chem. Rev., 1996, 96, 1105.
53. T. Honda and M. Kimura, Org. Lett., 2000, 2, 3925.
54. G. Lognay, J. L. Hemptinne, F. Y. Chan, CH. Gasper, M. Marlier, J. C. Braekman, D. Daloze, and J. M. Pasteels, J. Nat. Prod., 1996, 59, 510.
55. N. Yamazaki, T. Ito, and C. Kibayashi, Tetrahedron Lett., 1999, 40, 739.
56. (a) F. Broeders, J. C. Braekman, and D. Daloze, D. Bull. Soc. Chim. Belg., 1997, 106, 377;
57. (b) N. Yamazaki, T. Ito, and C. Kibayashi, Synlett, 1999, 37;
58. (c) D. J. Wardrop, C. L. Landrie, and J. A. Ortiz, Synlett, 2003, 1352.
59. J. S. Peterson, G. Fels, and H. Rapoport, J. Am. Chem. Soc., 1984, 106, 4539.
60. M. Roth, P. Dubs, E. Götschi, and A. Eschenmoser, Helv. Chim. Acta, 1971, 54, 710.
61. For Michael addition of Grignard reagent to enaminones, see: D. L. Comins, D. H. LaMunyon, and X. Chen, J. Org. Chem., 1997, 62, 8182.
62. A small amount of uncyclized δ-amino ester could also be isolated from this reaction; however, the uncyclized compound was easily transformed to the cyclization product by heating in benzene or by standing at room temperature for few days. The yield was demonstrated as the combined yield.
63. (a) M. Katoh, R. Matsyne, H. Nagase, and T. Honda, Tetrahedron Lett., 2004, 45, 6221;
64. (b) M. Katoh, R. Matsune, and T. Honda, Heterocycles, 2006, 67, 189.
65. (a) J. B. Koepfli, J. F. Mead, and J. A. Brockman, Jr., J. Am. Chem. Soc., 1947, 69, 1837;
66. (b) J. B. Koepfli, J. F. Mead, and J. A. Brockman, Jr., J. Am. Chem. Soc., 1949, 71, 1048;
67. (c) K. Murata, F. Takeno, S. Fushiya, and Y. Oshima, J. Nat. Prod., 1998, 61, 729.
68. (a) C. S. Jang, F. Y. Fu, C. Y. Wang, K. C. Huang, G. Lu, and T. C. Thou, Science, 1946, 103, 59;
69. T.-Q. Chou, F. Y. Fu, and Y. S. Kao, J. Am. Chem. Soc., 1948, 70, 1765;
70. (c) A. K. Frederick, Jr., C. F. Spencer, and K. Folkers, J. Am. Chem. Soc., 1948, 70, 2091;
71. (d) Y. Takaya, H. Tasaka, T. Chiba, K. Uwai, M. Tanitsu, H.-S. Kim, Y. Wataya, M. Miura, M. Takeshita, and Y. Oshima, J. Med. Chem., 1999, 42, 3163;
72. (e) H. Kikuchi, H. Tasaka, S. Hirai, Y. Takaya, Y. Iwabuchi, H. Ooi, S. Hatakeyama, H.-S. Kim, Y. Wataya, and Y. Oshima, J. Med. Chem., 2002, 45, 2563;
73. (f) S. Hirai, H. Kikuchi, H.-S. Kim, K. Begum, Y. Wataya, H. Tasaka, Y. Miyazawa, K. Yamamoto, and Y. Oshima, J. Med. Chem., 2003, 46, 4351.
74. S. Kobayashi, M. Ueno, R. Suzuki, and H. Ishitani, Tetrahedron Lett., 1999, 40, 2175.
75. For recent syntheses of febrifugine and/or isofebrifugine, see: (a) L. E. Burgess, E. K. M. Gross, and J. Jurka, Tetrahedron Lett., 1996, 37, 3255;
76. (b) S. Kobayashi, M. Ueno, R. Suzuki, H. Ishitani, H.-S. Kim, and Y. Wataya, J. Org. Chem., 1999, 64, 6833;
77. (c) Y. Takeuchi, H. Abe, and T. Harayama, Chem. Pharm. Bull., 1999, 47, 905;
78. (d) Y. Takeuchi, M. Hattori, H. Abe, and T. Harayama, Synthesis, 1999, 1814;
79. (e) Y. Takeuchi, K. Azuma, M. Takakura, H. Abe, and T. Harayama, Chem. Commun., 2000, 1643;
80. (f) O. Okitsu, R. Suzuki, and S. Kobayashi, Synlett, 2000, 989;
81. (g) T. Taniguchi and K. Ogasawara, Org. Lett., 2000, 2, 3193;
82. (h) Y. Takeuchi, K. Azuma, K. Takakura, H. Abe, H.-S. Kim, Y. Wataya, and T. Harayama, Tetrahedron, 2001, 57, 1213;
83. (i) H. Ooi, A. Urushibara, T. Esumi, Y. Iwabuchi, and S. Hatakeyama, Org. Lett., 2001, 3, 953;
84. (j) M. Sugiura and S. Kobayashi, Org. Lett., 2001, 3, 477;
85. (k) M. Sugiura, H. Hagio, R. Hirabayashi, and S. Kobayashi, J. Org. Chem., 2001, 66, 809;
86. (l) M. Sugiura, H. Hagio, R. Hirabayashi, and S. Kobayashi, J. Am. Chem. Soc., 2001, 123, 12510;
87. (m) P.-Q. Huang, B.-G. Wei, and Y.-P. Ruan, Synlett, 2003, 1663.
88. X. Zhang, A. C. Schmitt, and W. Jiang, Tetrahedron Lett., 2001, 42, 5335.
89. C. Nájera and M. Yus, Tetrahedron: Asymmetry, 1999, 10, 2245 and references cited therein.
90. (a) I. Collado, J. Ezquerra, J. J. Vaquero, and C. Pedregal, Tetrahedron Lett., 1994, 35, 8037;
91. (b) J. Mulzer, F. Schülzchen, and J.-W. Bats, Tetrahedron, 2000, 56, 4289.
92. F. N. Tebbe, G. W. Parshall, and G. S. Reddy, J. Am. Chem. Soc., 1978, 100, 3611.
93. (a) M. Katoh, H. Mizutani, and T. Honda, Tetrahedron Lett., 2005, 46, 5161;
94. (b) M. Katoh, H. Mizutani, and T. Honda, Heterocycles, 2006, 69, 193.
95. For recent reviews of synthesis and biological activity, see: (a) A. E. Nemr, Tetrahedron, 2000, 56, 8579;
96. (b) N. Asano, R. J. Nash, R. J. Molyneux, and G. W. J. Fleet, Tetrahedron: Asymmetry, 2000, 11, 1645;
97. (c) P. Sears and C.-H. Wong, Angew. Chem., Int. Ed., 1999, 38, 2300;
98. (d) J. P. Michael, Nat. Prod. Rep., 1999, 16, 675;
99. (e) J. P. Michael, Nat. Prod. Rep., 2000, 17, 579;
100. (f) J. P. Michael, Nat. Prod. Rep., 2001, 18, 520;
101. (g) J. P. Michael, Nat. Prod. Rep., 2002, 19, 719;
102. (h) J. P. Michael, Nat. Prod. Rep., 2003, 20, 458;
103. (i) J. P. Michael, Nat. Prod. Rep., 2004, 21, 625;
104. (j) J. P. Michael, Nat. Prod. Rep., 2005, 22, 603;
105. (k) A. D. Elbein and R. J. Molyneux, In Iminosugars as Glycosidase Inhibitors, ed. by A. E. Stutz, Wiley-VCH: Weinheim, Germany, 1999; p. 216;
106. (l) H. Takahata and T. Momose, In The Alkaloids, ed. by G. A. Cordell, Academic: San Diego, CA, 1993; Vol. 44, Chapter 3;
107. (m) A. D. Elbein and R. Molyneux, In Alkaloids: Chemical and Biological Perspectives; ed. by S. W. Pelletier, Wiley and Sons: New York, 1987; Vol. 5;
108. (n) N. Toyooka and H. Nemoto, Trends in Heterocyclic Chemistry, 2002, 8, 145.
109. S. C. Nigam, A. Mann, M. Taddei, and C. G. Wermuth, Synth. Commun., 1989, 19, 3139.
110. G. Bartoli, M. Bosco, M. Locatelli, E. Marcantoni, P. Melchiorre, and L. Sambri, Org. Lett., 2005, 7, 427.
111. (a) R. Appel, Angew. Chem., Int. Ed. Engl., 1975, 14, 801;
112. (b) Y. Shishido and C. Kibayashi, J. Org. Chem., 1992, 57, 2876.
113. H. K. Lee, J. S. Chun, and S. P. Chwang, J. Org. Chem., 2003, 68, 2471.
114. For reviews on catalytic metathesis, see: (a) R. H. Grubbs, S. J. Miller, and G. C. Fu, Acc. Chem. Res., 1995, 28, 446;
115. (b) H.-G. Schrnalz, Angew. Chem., Int. Ed. Engl., 1995, 34, 1833;
116. (c) M. Schuster and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 2036;
117. (d) S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371;
118. (e) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413;
119. (f) R. R. Schlock, Tetrahedron, 1999, 55, 8141;
120. (g) A. J. Phillips and A. D. Abell, Aldrichim. Acta, 1999, 32, 75;
121. (h) A. Fürstner, Angew. Chem. Int. Ed., 2000, 39, 3012;
122. (i) T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18;
123. (j) A. H. Hoveyda and R. R. Schrock, Chem. Eur. J., 2001, 7, 945;
124. (k) R. R. Schrock and A. H. Hoveyda, Angew. Chem. Int. Ed., 2003, 42, 4592.
125. M. G. M. D'Oca, R. A. Pilli, and I. Vencato, Tetrahedron Lett., 2000, 41, 9709.
126. M. Miyazawa, K. Yoshio, Y. Ishikawa, and H. Kameoka, J. Agric. Food Chem., 1998, 46, 1059.
127. L. Zhang, Y. Huang, Y. Qian, and P. Xiao, Zhongguo Yixue Kexueyuan Xuebao, 1995, 17, 343.
128. Y. Suzuki, K. Taguchi, Y. Hagiwara, K. Kajiyama, and T. Ikeda, Jpn. J. Pharmacol., 1981, 31, 653.
129. H. Matsuda, T. Morikawa, M.; Oda, Y. Asao, and M. Yoshikawa, Bioorg. Med. Chem. Lett., 2003, 13, 4445.
130. (a) S. Yasuda, M. Hanaoka, and Y. Arata, Chem. Pharm. Bull., 1980, 28, 831;
131. (b) Y. C. Hwang and F. W. Fowler, J. Org. Chem., 1985, 50, 2719;
132. (c) Y. C. Hwang, M. Chu, and F. W. Fowler, J. Org. Chem., 1985, 50, 3885.
133. (a) W. J. Moran, K. M. Goodenough, P. Raubo, and J. P. A. Harrity, Org. Lett., 2003, 5, 3427;
134. (b) K. M. Goodenough, W. J. Moran, P. Raubo, and J. P. A. Harrity, J. Org. Chem., 2005, 70, 207.
135. (a) H. Bredereck, G. Simchen, S. Rebsdat, W. Kantlehner, P. Horn, R. Wahl, H. Hoffman, and P. Grieshaber, Chem. Ber., 1968, 101, 41;
136. (b) S. Danishefsky, E. Berman, L. A. Clizbe, and M. Hirama, J. Am. Chem. Soc., 1979, 101, 4385.
137. (a) J.-M. Nuzilland, A. Boumendjel, and G. Massiot, Tetrahedron Lett., 1989, 30, 3779;
138. (b) D. F. Netz and J. L. Seidel, Tetrahedron Lett., 1992, 33, 1957.
139. T. Honda, R. Takahashi, and H. Namiki, J. Org. Chem., 2005, 70, 499.
140. (a) S. Ohmiya, K. Saito, and I. Murakoshi, Lupine Alkaloids. In The Alkaloids; ed. by G. A. Cordell, Academic Press: New York, 1995; Vol. 47, p. 1;
141. (b) A. El-Shazly, T. Sarg, A. Ateya, E. A. Witte, and M. Wink, Pharmazie, 1996, 51, 768.
142. (a) A. Partheil, Arch. Pharm. (Weinheim), 1894, 232, 161;
143. (b) H. R. Ing, J. Chem. Soc., 1932, 2778;
144. (c) N. J. Leonard, In The Alkaloids; ed. by R. H. F. Manske and H. L. Holmes, Academic Press: New York, 1953; Vol. 3, pp. 119-199.
145. (a) E. E. van Tamelen and J. S. Baran, J. Am. Chem. Soc., 1955, 77, 4944;
146. (b) E. E. van Tamelen and J. S. Baran, J. Am. Chem. Soc., 1956, 78, 2913;
147. (c) E. E. van Tamelen and J. S. Baran, J. Am. Chem. Soc., 1958, 80, 4659;
148. (d) F. Bohlmann, A. English, N. Ottawa, H. Sander, and W. Weise, Chem. Ber., 1956, 89, 792;
149. (e) T. R. Govindachari, S. Rajadurai, M. Subramanian, and B. S. Thyagarajan, J. Chem. Soc., 1957, 3839.
150. For recent synthesis of racemic cytisine, see: (a) P. Nshimyumukiza, D. Cahard, J. Rouden, M.-C. Lasne, and J.-C. Plaquevent, Tetrahedron Lett., 2001, 42, 7787;
151. (b) B. T. O'Neill, D. Yohannes, M. W. Bundesmann, and E. P. Arnold, Org. Lett., 2000, 2, 4201;
152. (c) J. W. Coe, Org. Lett., 2000, 2, 4205;
153. (d) C. Botuha, C. M. S. Galley, and T. Gallagher, Org. Biomol. Chem., 2004, 2, 1825 and references therein.
154. For chiral synthesis of (-)-cytisine, see: (e) B. Danieli, G. Lesma, D. Passarella, A. Sacchetti, A. Silvani, and A. Virdis, Org. Lett., 2004, 6, 493.
155. (a) R. B. Barlow and L. J. McLeod, Br. J. Pharmacol., 1969, 35, 161;
156. (b) I. A. McDonald, N. Cosford, and J.-M. Vernier, Annual Reports in Medicinal Chemistry; Academic Press: New York, 1994; Vol. 30, p. 41;
157. (c) J. D. Schmitt and M. Bencherif, Annual Reports in Medicinal Chemistry; Academic Press: New York, 2000; Vol. 35, p. 41.
158. (a) L. A. Pabreza, S. Dhawan, and K. J. Keller, Mol. Pharmacol., 1991, 39, 9;
159. (b) M. Hall, L. Zerbe, S. Leonard, and R. Freedman, Brain Res., 1993, 600, 127;
160. (c) H. K. Happe, J. L. Peters, D. A. Bergman, and L. C. Murrin, Neuroscience, 1994, 62, 929.
161. I. Murakoshi, E. Kidoguchi, J. Haginiwa, S. Ohmiya, K. Higashiyama, and H. Otomasu, Phytochemistry, 1981, 20, 1407. Kuraramine was isolated as an amorphous solid.
162. P. Máximo and A. Lourencüo, J. Nat. Prod., 2000, 63, 201.
163. I. Murakoshi, E. Kidoguchi, J. Haginiwa, S. Ohmiya, K. Higashiyama, and H. Otomasu, Phytochemistry, 1982, 21, 2379. The optical rotation has not been reported, due to the small amount available.
164. A. M. P. Koskinen, J. Schwerdtfeger, and M. Edmonds, Tetrahedron Lett., 1997, 38, 5399.
165. (a) C. González, E. Guilián, and L. Castedo, Tetrahedron, 1999, 55, 5195;
166. (b) M. Adamczyk, S. R. Akireddy, and R. E. Reddy, Org. Lett., 2000, 2, 3421;
167. (c) J. E. Baldwin, R. M. Adlington, A. Conte, N. R. Irtapati, R. Marquez, and G. J. Pritchard, Org. Lett., 2002, 4, 2125.
168. Although the value of the optical rotation of ent-87 was slightly lower than that in the literature, we believe that our synthetic compound is optically pure, since the intermediate 96 was successfully transformed into cytisine with the correct optical rotation.
169. Y.-H. Wang, J.-S. Li, H. Kubo, K. Higashiyama, H. Komiya, and S. Ohmiya, Chem. Pharm. Bull., 1999, 47, 1308.
170. M. Normatov, K. A. Abduazimov, and S. Y. Yunusov, Dokl. Akad. Nauk UzSSR, 1962, 19, 45.
171. (a) M. Katoh, H. Inoue, A. Suzuki, and T. Honda, Synlett, 2005, 2820;
172. (b) M. Katoh, H. Inoue, and T. Honda, Heterocycles, 2007, 72, 497.
173. K. Hayashi, K. Nunami, K. Sakai, Y. Ozaki, J. Kato, K. Kinashi, and N. Yoneda, Chem. Pharm. Bull., 1983, 31, 3553.
174. N. Gulavita, A. Hori, Y. Shimizu, P. Laszlo, and J. Clardy, Tetrahedron Lett., 1988, 29, 4381.
175. T. Honda, A. Yamamoto, Y. Cui, and M. Tsubuki, J. Chem. Soc., Perkin Trans. 1, 1992, 531.
176. K. O. Hallinan and T. Honda, Tetrahedron, 1995, 51, 12211.
177. Synthesis of (-)- and racemic aphanorphine: (a) S. Takano, K. Inomata, T. Sato, M. Takahashi, and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1990, 290;
178. (b) A. N. Hulme, S. S. Henry, and A. I. Meyers, J. Org. Chem., 1995, 60, 1265;
179. (c) A. I. Meyers, W. Schmidt, and B. Santiango, Heterocycles, 1995, 40, 525;
180. (d) A. Fadal and O. Arzel, Tetrahedron: Asymmetry, 1995, 6, 893;
181. (e) M. Node, H. Imazato, R. Kurosaki, Y. Kawano, T. Inoue, K. Nishide, and K. Fuji, Heterocycles, 1996, 42, 811;
182. (f) S. Shiotani, H. Okada, K. Nakamata, T. Yamamoto, and F. Sekino, Heterocycles, 1996, 43, 1031;
183. (g) A. Fadal and O. Arzel, Tetrahedron:Asymmetry, 1997, 8, 371;
184. (h) M. Shimizu, T. Kamikubo, and K. Ogasawara, Heterocycles, 1997, 46, 21;
185. (i) K. Tanaka, T. Taniguchi, and K. Ogasawara, Tetrahedron Lett., 2001, 42, 1049;
186. (j) O. Tamura, T. Yanagimachi, T. Kobayashi, and H. Ishibashi, Org. Lett., 2001, 3, 2427;
187. (k) A. S. ElAzab, T. Taniguchi, and K. Ogasawara, Heterocycles, 2002, 56, 39;
188. (l) S. K. Taylor, M. Ivanovic, L. J. Simons, and M. M. Davis, Tetrahedron:Asymmetry, 2003, 14, 743;
189. (m) Y. 44 HETEROCYCLES, Vol. 83, No. 1, 2011
190. Kita, J. Futamura, Y. Ohba, Y. Sawama, J. K. Genesh, and H. Fujioka, J. Org. Chem., 2003, 68, 8268;
191. (n) O. Tamura, T. Yanagimachi, and H. Ishibashi, Tetrahedron:Asymmetry, 2003, 14, 3033;
192. (o) T. Yoshimitsu, C. Atsumi, E. Iimori, H. Nagaoka, and T. Tanaka, Tetrahedron Lett., 2008, 49, 4473.
193. J. R. Fuchs and R. L. Funk, Org. Lett., 2001, 3, 3923.
194. J. Jurczak, D. Gryko, E. Kobrzycka, H. Gruza, and P. Prokopowicz, Tetrahedron, 1998, 54, 6051.
195. (a) A. R. Katritzky, X. Lan, J. Z. Yang, and O. V. Denisko, Chem. Rev., 1998, 98, 409;
196. (b) A. R. Katritzky, J. Cobo-Domingo, B. Yang, and P. J. Steel, Tetrahedron:Asymmetry, 1999, 10, 255;
197. (c) O. Koepler, S. Laschat, A. Baro, P. Fischer, B. Miehlich, M. Horfilder, and C. le Viseur, Eur. J. Org. Chem., 2004, 3611.
198. S. Takano, K. Inomata, T. Sato, and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1989, 1591.
199. T. Honda, E. Aranishi, and K. Kaneda, Org. Lett., 2009, 11, 1857.
200. (a) G. Blasko, In The Alkaloids; ed. by A. Brossi, Academic Press Inc.: New York, 1990; p. 157;
201. (b) T. B. Lee, Illustrated Flora of Korea; Hanygmoonsa: Seoul, 1989; p. 385.
202. J. Fidalgo, L. Castedo, and D. Dominguez, Tetrahedron Lett., 1993, 34, 7317.
203. (a) G. Blasko, S. F. Hussain, A. J. Freyer, and M. Shamma, Tetrahedron Lett., 1981, 22, 3127;
204. (b) N. Murugesan, G. Blasko, R. D. Minard, and M. Shamma, Tetrahedron Lett., 1981, 22, 3131;
205. (c) G. Blasko, N. Murugesan, S. F. Hussain, R. D. Minard, M. Shamma, B. Sener, and M. Tanker, Tetrahedron Lett., 1981, 22, 3135;
206. (d) G. Blasko, N. Murugesan, A. J. Freyer, D. J. Gula, B. Sener, and M. Shamma, Tetrahedron Lett., 1981, 22, 3139;
207. (e) G. Blasko, N. Murugesan, A. J. Freyer, R. D. Minard, and M. Shamma, Tetrahedron Lett., 1981, 22, 3143.
208. G. I. Yakimov, N. M. Mollov, J. E. Leet, H. Guinaudeau, A. J. Freyer, and M. Shamma, J. Nat. Prod., 1984, 47, 1048.
209. G. Blasko, Acta Chim. Hung., 1991, 128, 819.
210. For transformation to protopine alkaloid, see: (a) K. Orito and M. Itoh, J. Chem. Soc., Chem. Commun., 1978, 812;
211. (b) K. Orito, Y. Kurokawa, and M. Itoh, Tetrahedron, 1980, 36, 617;
212. (c) Y. Wada, H. Kaga, S. Uchiito, E. Kumazawa, M. Tomiki, Y. Onozaki, N. Kurono, M. Tokuda, T. Ohkuma, and K. Orito, J. Org. Chem., 2007, 72, 7301.
213. For transformation to rhoeadine alkaloid, see: (d) K. Orito, R. H. Manske, and R. Rodrigo, J. Am. Chem. Soc., 1974, 96, 1944;
214. (e) M. Hanaoka, M. Inoue, N. Kobayashi, and S. Yasuda, Chem. Pharm. Bull., 1987, 35, 980.
215. M. W. Giese and W. H. Moser, J. Org. Chem., 2005, 70, 6222.
216. For photochemical synthesis of benzindenoazepine ring system, see: (a) J. Fidalgo, L. Castedo, and D. Dominguez, Heterocycles, 1994, 39, 581.
217. For a radical cyclization approach, see ref 2. For transformation of protoberberines to benzindenoazepines, see: (b) M. Hanaoka, M. Iwasaki, S. Sakurai, and C. Mukai, Tetrahedron Lett., 1983, 24, 3845;
218. (c) M. Hanaoka, A. Ashimori, H. Yamagishi, and S. Yasuda, Chem. Pharm. Bull., 1983, 31, 2172;
219. (d) M. Hanaoka, S. K. Kim, M. Inoue, K. Nagami, Y. Shimada, and S. Yasuda, Chem. Pharm. Bull., 1985, 33, 1434.
220. I. Matsuo, T. Takahashi, and S. Oki, Yakugaku Zasshi, 1964, 84, 711.
221. The deethoxycarbonyl analogue of 128 was generated as a byproduct under these reaction conditions.
222. L. A. Mitscher, D. L. Flynn, H. E. Gracey, and S. D. Drake, J. Med. Chem., 1979, 22, 1354.
223. (a) T. Honda and C. Hisa, Tetrahedron Lett., 2009, 50, 4654;
224. (b) T. Honda and C. Hisa, Heterocycles, 2010, 80, 1381.
225. (a) E. Hasegawa, K. Ishiyama, T. Fujita, T. Kato, and T. Abe, J. Org. Chem., 1997, 62, 2396;
226. (b) G. E. Keck, C. A. Wager, T. Sell, and T. T. Wager, J. Org. Chem., 1999, 64, 2172;
227. (c) A. Dahlën and G. Hilmersson, Chem. Eur. J., 2003, 9, 1123;
228. (d) P. R. Chopade, E. Prasad, and R. A. Flowers, J. Am. Chem. Soc., 2004, 126, 44;
229. (e) H. Farran and S. Shmaryahu Hoz, J. Org. Chem., 2009, 74, 2075;
230. (f) T. Ankner and G. Hilmersson, Org. Lett., 2009, 11, 1865.
231. B. S. Bal, W. E. Childers, Jr., and H. W. Pinnick, Tetrahedron, 1981, 37, 2091.
232. M. Katoh, C. Hisa, and T. Honda, Tetrahedron Lett., 2007, 48, 4691.