Synthesis of phthalideisoquinoline and protoberberine alkaloids and indolo[2,1-α]isoquinolines in a divergent route involving palladium(0)- catalyzed carbonylation

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6583-6596

  Orito, Kazuhiko ^a   Miyazawa, Mamoru ^a   Kanbayashi, Ryo ^a   Tokuda, Masao ^a   Suginome, Hiroshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; PALLADIUM; PROTOBERBERINE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032888524     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982451w     Document Type: Article

References (180)

1. This paper is subtitled "Benzolactams III".
2. For general reviews on carbonylation, see (a) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: Orlando, 1985; pp 341-400.
3. (b) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. In Carbonylation, Direct Synthesis of Carbonyl Compounds, Plenum Press: New York, 1991.
4. (c) Tsuji, J. In Palladium Reagents and Catalysts, Innovation in Organic Synthesis; John Wiley & Sons: New York, 1995.
5. For preparation of benzolactams, see: (a) Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684-1687.
6. (b) Ishikura, M.; Mori, M.; Terashima, M.; Ban, Y. Chem. Commun. 1982, 741-742.
7. (c) Mori, M.; Ishikura, M.; Ikeda, T.; Ban, Y. Heterocycles 1981, 16, 1491-1494.
8. (d) Ishikura, M.; Mori, M.; Ikeda, T.; Terashima, M.; Ban, Y. J. Org. Chem. 1982, 47, 2456-2461.
9. (e) Mori, M.; Ishikura, M.; Ikeda, T.; Ban, Y. Heterocycles 1984, 22, 253-256.
10. (f) Mori, M.; Purvaneckas, G.-E.; Ishikura, M.; Ban, Y. Chem. Pharm. Bull. 1984, 32, 3840-3847.
11. (g) Mori, M.; Uozumi, Y.; Kimura, M.; Ban, Y. Tetrahedron 1986, 42, 3793-3806.
12. (h) Y. Uozumi, Y.; Kawasaki, N.; Mori, E.; Shibasaki, M. J. Am. Chem. Soc. 1989, 111, 3725-3727.
13. (i) Pandey, G. D.; Tiwari, K. P. Synth. Commun. 1979, 9, 895-900.
14. (j) Pandey, G. D.; Tiwari, K. P. Tetrahedron 1981, 37, 1213-1214.
15. (k) Cacchi, S.; Fabrizi, G.; Malinelli, F. Synlett 1996, 997-998.
16. (l) Cho, C. S.; Lee, J. W.; Lee, D. U.; Shim, S. C.; Khim, T. J. Chem. Commun. 1996, 2115-2116.
17. For preparation of benzolactones, see (a) Mori, M.; Chiba, K.; Inotsume, N.; Ban, Y. Heterocycles 1979, 12, 921-924, and ref 3h.
18. (b) Coowel, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4193-4198.
19. (c) Martin, L. D.; Stille, J. K.; J. Org. Chem. 1982, 47, 3630-3633.
20. (c) Larock, R. C.; Fellow, C. A. J. Am. Chem. Soc. 1982, 104, 1900-1907.
21. Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972-6975.
22. Onto, K.; Miyazawa, M.; Suginome, H. Tetrahedron 1995, 51, 2489-2496.
23. For a preliminary report, see Orito, K.; Miyazawa, M.; Suginome, H. Synlett 1994, 245-246.
24. For a review, see MacLean, D. B. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1985; Vol. 24; pp 253-286.
25. For a review, see Blasko, G.; Gula, D. J.; Shamma, M. J. Nat. Products 1982, 45, 105-122.
26. (a) Kametani, T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley and Sons: New York, 1977; Vol. 3, pp 1-272.
27. (b) Rozwadowska, M. D. Heterocycles 1994, 39, 903-931.
28. For selected articles published on and after 1985: (a) Narasimhan, N. S.; Joshi, R. R.; Kusurkar, R. S. J. Chem. Soc., Chem. Commun. 1985, 177-178.
29. (b) Seebach, D.; Huber, I. M. P. Chimia 1985, 39, 233-234.
30. (c) Seebach, D.; Huber, I. M. P.; Syfrig, M. A. Helv. Chim. Acta 1987, 70, 1357-1377.
31. (d) Huber, T. M. P.; Seebach, D. Helv. Chim. Acta 1987, 70, 1944-1954.
32. (e) Rein, K. S.; Gawley, R. E. Tetrahedron Lett. 1990, 31, 3711-3714.
33. (f) Kessar, S. V.; Singh, P.; Vohra, R.; Kaur, N. P.; Singh, K. N. J. Chem. Soc., Chem. Commun. 1991, 568-570.
34. (g) Rein, K. S.; Gawley, R. E. J. Org. Chem. 1991, 56, 1564-1573.
35. (h) Gawley, R. E.; Zhang, P. J. Org. Chem. 1996, 61, 8103-8112.
36. (a) Moniot, J. L.; Shamma, M. J. Am. Chem. Soc. 1976, 98, 6714-6715; J. Org. Chem. 1979, 44, 4337-4342.
37. (a) Moniot, J. L.; Shamma, M. J. Am. Chem. Soc. 1976, 98, 6714-6715; J. Org. Chem. 1979, 44, 4337-4342.
38. (b) Moniot, J. L.; Abd el Rahman, A. H.; Shamma, M. Tetrahedron Lett. 1977, 3787-3790.
39. (c) Shamma, M.; Hindenlang, D. M.; Wu, T.-T.; Moniot, J. L. Tetrahedron Lett. 1977, 49, 4285-4288.
40. (a) Marshall, M. A.; Pyman, F. L.; Robinson, R. J. Chem. Soc. 1934, 1315-1320.
41. (b) Gaál, G.; Kerekes, P.; Bognár, R. J. Prakt. Chem. 1971, 315, 935-939.
42. (c) Gaál, G.; Kerekes, P.; Gorecki, P.; Bognár, R. Magy. Kém. Foly. 1971, 77, 286-289; Chem. Abstr. 1971, 75, 98702b.
43. (c) Gaál, G.; Kerekes, P.; Gorecki, P.; Bognár, R. Magy. Kém. Foly. 1971, 77, 286-289; Chem. Abstr. 1971, 75, 98702b.
44. (d) Gaál, G.; Kerekes, P.; Bognár, R. Magy. Kém. Foly. 1971, 77, 533-535; Chem. Abstr. 1972, 76, 25451e.
45. (d) Gaál, G.; Kerekes, P.; Bognár, R. Magy. Kém. Foly. 1971, 77, 533-535; Chem. Abstr. 1972, 76, 25451e.
46. (e) Teitel, S.; O'Brien, J.; Brossi, A. J. Org. Chem. 1972, 37, 1879-1881.
47. Orito, K.; Suginome, H.; De Silva, S. O.; Rodrigo, R. Heterocycles 1987, 26, 3077-3080.
48. (a) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009-3013.
49. (b) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818-1826.
50. DBU, pyridine, 4-(dimethylamino)pyridine, and 2,2,6,6-tetramethylpiperidine were also ineffective.
51. 3 did not work at all, and 5a was recovered unchanged.
52. (a) Chuit, C.; Foulon, J. P.; Normant, J. F. Tetrahedron Lett. 1980, 36, 2305-2310; 1981, 37, 1385-1389.
53. (a) Chuit, C.; Foulon, J. P.; Normant, J. F. Tetrahedron Lett. 1980, 36, 2305-2310; 1981, 37, 1385-1389.
54. (b) Bourgain-Commercon, M.; Foulon, J. P.; Normant, J. F. J. Organomet. Chem. 1982, 228, 321-326.
55. (c) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015-6018, 6019-6022.
56. (d) Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050.
57. (e) Horiguchi, Y.; Matsuzawa, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4025-4028.
58. (f) Nakamura, E.; Matsuzawa, S.; Horiguchi, Y. Kuwajima, I. Tetrahedron Lett. 1986, 27, 4029-4032.
59. (a) Gawronski, J. K. Tetrahedron Lett. 1984, 25, 2605-2608.
60. (b) Picotin, G.; Miginiac, P. J. Org. Chem. 1987, 52, 4796-4798; Tetrahedron Lett. 1987, 28, 4551-4554.
61. (b) Picotin, G.; Miginiac, P. J. Org. Chem. 1987, 52, 4796-4798; Tetrahedron Lett. 1987, 28, 4551-4554.
62. (c) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390-2392.
63. (d) Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5431-5438.
64. (e) Knochel, P.; Roozema, M. J.; Tucker, C.; Retherford, C.; Furlong, M. T.; AchyuthaRao, S. Pure Appl Chem. 1992, 64, 361-369.
65. (f) Takai, K.; Kakiuchi, T.; Uchimoto, K. J. Org. Chem. 1994, 59, 2671-2673.
66. Muzart, J.; Riahi, A. Synth. Commun. 1991, 21, 1247-1250.
67. Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37, 7049-7052.
68. Schneider, M. E.; Möhring, U.; Werner, H. J. Organomet. Chem. 1996, 520, 181-186.
69. Koide, K.; Ohno, M.; Kobayashi, S. Synthesis 1997, 1175-1176.
70. (a) Feghouli, A.; Fort, Y.; Vanderesse, R.; Caubùre, P. Tetrahedron Lett. 1988, 29, 1379-1382.
71. (b) Fort, Y.; Feghouli, A.; Vanderesse, R.; Caubùre, P. J. Org. Chem. 1990, 55, 5911-5915.
72. Ohkuma, T.; Hashiguchi, S.; Noyori, R. J. Org. Chem. 1994, 59, 217-221.
73. Effects of bulky amines as bases in a palladium(0)-catalyzed carbonylation were reported, see: Murahashi, S.; Imada, Y.; Taniguchi, Y.; Higashiura, S. J. Org. Chem. 1993, 58, 1538-1545.
74. Sinhababu, A. K.; Borchardt, R. T. J. Org. Chem. 1983, 48, 2356-2360.
75. (a) Martin, N. H.; Jefford, C. W. Helv. Chim. Acta 1981, 64, 2189-2192.
76. (b) Wert, K. L.; Chackalamannil, S.; Miller, E.; Dalton, D. R.; Zacharias, D. E.; Glusker, J. P. J. Org. Chem. 1982, 47, 5141-5150.
77. 4, such as that in an old bottle, was used for these reductions, the eryrtro-selectivity became lower.
78. (a) Moniot, J. L.; Shamma, M. J. Org Chem. 1979, 44, 4337-4342.
79. (b) McMahon, R. M.; Thornber, C. W. J. Chem. Soc., Perkin Trans. 1 1982, 2163-2167.
80. (a) Späth, E.; Epstein, H. Ber. 1926, 59, 2791-2800.
81. (b) Kupchan, S. M.; Kubota, S.; Fujita, E.; Kobayashi, S.; Block, J. H.; Telang, S. A. J. Am. Chem. Soc. 1966, 88, 4212-4218.
82. (c) Reference 35b.
83. 2, or CuI in boiling toluene, oxidative cleavages of 19j, the debromo derivative of 19a, and N-methylephedrine were also observed.
84. (a) Cram, J. D.; Abd Elhafez, F. A. J. Am Chem. Soc. 1952, 74, 5828-5835.
85. (b) Cram, D. J.; Wilson, D. R. J. Am. Chem. Soc. 1963, 85, 1245-1249.
86. Kerekes, P.; Gaál, G.; Bognár, R.; Töró, T.; Costisella, B. Acta Chim. Acad. Sci. Hung. 1980, 105, 283-291.
87. Clarke, S. I.; Kasum, B.; Prager, R. H.; Ward, A. D. Aust. J. Chem. 1988, 36, 2493-2498.
88. For a preliminary report, see Orito, K.; Miyazawa, M.; Suginome, H. Heterocycl. Commun. 1995, 1, 239-240.
89. Ewing, J.; Hughes, G. K.; Ritchie, E.; Taylor, W. C. Nature 1952, 169, 618-619; Aust J. Chem. 1953, 6, 78-85.
90. Ewing, J.; Hughes, G. K.; Ritchie, E.; Taylor, W. C. Nature 1952, 169, 618-619; Aust J. Chem. 1953, 6, 78-85.
91. Elliott, I. W. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1987; Vol. 31; pp 101-116.
92. (a) Kametani, T.; Ogasawara, K. J. Chem. Soc. (C) 1967, 2208-2212.
93. (b) Benington, F.; Morin, R. D. J. Org. Chem. 1967, 32, 1050-1053.
94. (c) Kametani, T.; Fukumoto, K.; Nakano, T. J. Heterocycl. Chem. 1972, 9, 1363-1366.
95. (d) Kametani, T.; Shibuya, S.; Kano, S. J. Chem. Soc., Perkin Trans. 1 1973, 1212-1214.
96. (e) Ahmad, I.; Gibson, M. Can. J. Chem. 1975, 53, 3660-3664.
97. (f) Kessar, S. V.; Batra, S.; Nadir, U. K.; Gandhi, S. S. Ind. J. Chem. 1975, 13, 1109-1112.
98. (g) Mak, C.-P.; Brossi, A. Heterocycles 1979, 12, 1413-1416.
99. (h) Ambros, R.; von Angerer, S.; Wiegrebe, W. Arch. Pharm. 1988, 321, 481-486.
100. (i) Meyers, A. I.; Sielecki, T. M. J. Am. Chem. Soc. 1991, 113, 2789-2790.
101. (a) Robinson, R.; Sugasawa, S. J. Chem. Soc. 1932, 798-805.
102. (b) Harley-Mason, J. J. Chem. Soc. 1953, 1465-1466.
103. (c) Hess, U.; Hiller, K.; Schroeder, R. S. J. Prakt. Chem. 1977, 319, 568-572.
104. Ninomiya, I.; Yasui, J.; Kiguchi, T. Heterocycles 1977, 6, 1855-1860.
105. Takano, S.; Satoh, S.; Ogasawara, K. Heterocycles 1987, 26, 1483-1485.
106. (a) Mathew, K. K.; Menon, K. N. Proc. Indian Acad. Sci. 1949, 29A, 361-363.
107. (b) Yasuda, S.; Hirasawa, T.; Yoshida, S.; Hanaoka, M. Chem. Pharm. Bull. 1989, 37, 1682-1683.
108. An alternative reaction pathway (i → ii → iii) with a leaving group X on a nitrogen-containing ring system 3, based on the thermal electrocyclization of a pentadienyl anion to a cyclopentenyl anion, cannot be discarded. For selected references, see Stapp, P. R.; Kieinschmidt, R. F. J. Org. Chem. 1965, 30, 3006-3009; Slaugh, L. H. J. Org. Chem. 1967, 32, 108-113; Bates, R. B.: McCombs, D. A. Tetrahedron Lett. 1969, 977-978; Shoppee, C. W.; Henderson, G. N. J. Chem. Soc., Perkin Trans. 1 1975, 765-772. Formula represented
109. An alternative reaction pathway (i → ii → iii) with a leaving group X on a nitrogen-containing ring system 3, based on the thermal electrocyclization of a pentadienyl anion to a cyclopentenyl anion, cannot be discarded. For selected references, see Stapp, P. R.; Kieinschmidt, R. F. J. Org. Chem. 1965, 30, 3006-3009; Slaugh, L. H. J. Org. Chem. 1967, 32, 108-113; Bates, R. B.: McCombs, D. A. Tetrahedron Lett. 1969, 977-978; Shoppee, C. W.; Henderson, G. N. J. Chem. Soc., Perkin Trans. 1 1975, 765-772. Formula represented
110. An alternative reaction pathway (i → ii → iii) with a leaving group X on a nitrogen-containing ring system 3, based on the thermal electrocyclization of a pentadienyl anion to a cyclopentenyl anion, cannot be discarded. For selected references, see Stapp, P. R.; Kieinschmidt, R. F. J. Org. Chem. 1965, 30, 3006-3009; Slaugh, L. H. J. Org. Chem. 1967, 32, 108-113; Bates, R. B.: McCombs, D. A. Tetrahedron Lett. 1969, 977-978; Shoppee, C. W.; Henderson, G. N. J. Chem. Soc., Perkin Trans. 1 1975, 765-772. Formula represented
111. An alternative reaction pathway (i → ii → iii) with a leaving group X on a nitrogen-containing ring system 3, based on the thermal electrocyclization of a pentadienyl anion to a cyclopentenyl anion, cannot be discarded. For selected references, see Stapp, P. R.; Kieinschmidt, R. F. J. Org. Chem. 1965, 30, 3006-3009; Slaugh, L. H. J. Org. Chem. 1967, 32, 108-113; Bates, R. B.: McCombs, D. A. Tetrahedron Lett. 1969, 977-978; Shoppee, C. W.; Henderson, G. N. J. Chem. Soc., Perkin Trans. 1 1975, 765-772. Formula represented
112. (a) See ref 3 cited in ref 48i. (b) See ref 12 cited in ref 48i.
113. See ref 1 cited in ref 48i.
114. Narasimhan, N. S.; Mali, R. S.; Kulkarni, B. K. Tetrahedron 1983, 33, 1975-1982.
115. For reviews, see (a) Kametani, T.; Ihara, M. Heterocycles 1979, 13, 497-530.
116. (b) Pandey, G. D.; Tiwari, K. P. Heterocycles 1980, 14, 59-82.
117. (c) Bhakuni, D. S.; Jain, S. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1986; Vol. 28; pp 95-171.
118. Selected articles published on and after 1986; Synthesis based on the modified Pictet-Spengler, Bischler-Napieralski, or Pomerantz-Fritsch reaction, see (a) Czarnocki, Z.; Maclean, D. B.; Szarek, W. A. Bull. Soc. Chim. Belg. 1986, 95, 749-769.
119. (b) Orito, K. Matsuzaki, T.; Suginome, H. Org. Prep. Proc. Int. 1989, 21, 309-314.
120. (c) Sotomayor, N.; Domínguez, E.; Lete, E. Synlett 1993, 431-433.
121. (d) Czarnocki, Z.; Maclean, D. B.; Szarek, W. A. J. Chem. Res. (C) 1992, 234-335; J. Chem. Res. (M) 1992, 2801-2819.
122. (d) Czarnocki, Z.; Maclean, D. B.; Szarek, W. A. J. Chem. Res. (C) 1992, 234-335; J. Chem. Res. (M) 1992, 2801-2819.
123. (e) Commins, D. L.; Thakker, P. M.; Baevsky, M. F. Tetrahedron 1997, 53, 16327-16340.
124. Synthesis based on nucleophilic addition of carbanions to 3,4-dihydroisoquinolines, see (f) Warrener, R. N.; Lin, L.; Russell, R. A. Tetrahedron 1988, 54, 7485-7496.
125. (g) Pyne, G. S.; Branko, D. J. Org. Chem. 1900, 55, 1932-1936.
126. (h) Kessar, S. V.; Singh, P.; Vohra, R.; Kaur, N. P.; Venugopal, D. J. Org. Chem. 1992, 57, 6716-6720.
127. Synthesis based on alkylation on a C-1 metalated tetrahydroisoquinoline, see (i) Matulenko, M. A.; Meyers, A. I. J. Org. Chem. 1996, 61, 573-580.
128. Synthesis based on photochemical cyclization of enamides, see (j) Weimar, C.; von Angerer, S.; Wiegrebe, W. Arch. Pharm. 1991, 324, 907-912.
129. Synthesis based on radial cyclization, see (k) Dai-Ho, G.; Mariano, P. S. J. Org. Chem. 1987, 52, 706-707.
130. (l) Takano, S.; Suzuki, M.; Ogasawara, K. Heterocycles 1990, 31, 1151-1156.
131. (m) Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315-2318.
132. (n) Nimgirawath, S.; Ponghusabun, O.-a. Aust. J. Chem. 1994, 47, 951-955.
133. Synthesis based on cycloaddition reaction of isoquinoline-pyrroline-2,3-dione with benzyne, see (o) Cobas, A.; Guitián, E.; Castedo, L. J. Org. Chem. 1992, 57, 6765-6769.
134. Synthesis based on palladium-catalyzed cyclization, see (p) Bombrun, A.; Sageot, O. Tetrahedron Lett. 1997, 38, 1057-1060.
135. Trifonov, L. S.; Orehovats, A. S. Tetrahedron Lett. 1985, 26, 3159-3162.
136. Cushman, M.; Dekow, F. W. J. Org. Chem. 1979, 44, 407-409.
137. Iwasa, K.; Gupta, Y. P.; Cushman, M. J. Org. Chem. 1981, 46, 4744-4750.
138. Asymmetric reduction of imines 15-17 is under investigation, and the results will be reported later.
139. Cava, M. P.; Mitchel, M. J.; Havlicek, S. C.; Lindert, A.; Spangler, R. J. I. J. Org. Chem. 1970, 35, 1175-1179.
140. Cava, M. P.; Stern, P.; Wakisaka, K. Tetrahedron 1973, 29, 2245-2249.
141. Prager, R. H.;Trippett, J. M.; Ward, A. D. Aust. J. Chem. 1981, 34, 1085-1093.
142. Smula, V.; Cundasawmy, N. E.; Holland, H. L.; MacLean, D. B. Can. J. Chem. 1973, 51, 3287-3293.
143. Haworth, R. D.; Pinder, A. R. J. Chem. Soc. 1950, 1776-1780.
144. Shono, T.; Usui, Y.; Hamaguchi, H. Tetrahedron Lett. 1980, 21, 1351-1354.
145. Kametani, T.; Honda, T.; Inoue, H.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1976, 1221-1225.
146. Nalliah, B.; MacLean, D. B.; Rodrigo, R. G. A.; Manske, R. H. Can. J. Chem. 1977, 55, 922-924.
147. Nalliah, B.; MacLean, D. B.; Holland, H. L.; Rodrigo, R. Can. J. Chem. 1979, 57, 1545-1578.
148. Slemon, C. E.; Hellwig, L. C.; Ruder, J.-P.; Hoskins, E. W.; MacLean, D. B. Can. J. Chem. 1981, 59, 3055-3060.
149. Wheley, W. M.; Meadow, M. J. Chem. Soc. 1953, 1067-1070.
150. Seitanidi, K. L.; Yagudaev, M. R.; Israilov, I. A.; Yunusov, M. S. Khim. Prirodu. Soedin. 1978, 465-471; Chem. Abstr. 1979, 90, 6585z.
151. Seitanidi, K. L.; Yagudaev, M. R.; Israilov, I. A.; Yunusov, M. S. Khim. Prirodu. Soedin. 1978, 465-471; Chem. Abstr. 1979, 90, 6585z.
152. Hope, E. Pyman, F. L. Remfry, F. G. P.; Robinson, R. J. Chem. Soc. 1931, 236-247.
153. Haworth, R. D.; Pinder, A. R.; Robinson, R. Nature 1950, 165, 529.
154. Shono, K.; Hamaguchi, H.; Sasaki, M.; Figita, S.; Nagami, K. J. Org. Chem. 1983, 48, 1621-1628.
155. Groenewoud, P. W. G.; Robinson, R. J. Chem. Soc. 1936, 199-202.
156. Mehra, K.; Garg, H. S.; Bhakuni, D. S.; Khanna, N. M. Ind. J. Chem. 1976, 14B, 844-848.
157. Shamma, M.; Georgiev, V. St. Tetrahedron Lett. 1974, 27, 2339-2342; Tetrahedron 1976, 32, 211-215.
158. Shamma, M.; Georgiev, V. St. Tetrahedron Lett. 1974, 27, 2339-2342; Tetrahedron 1976, 32, 211-215.
159. Kametani, T.; Ohsawa, T.; Hirata, S.; Premila, S. M.; Ihara, M.; Fukumoto, K. Chem. Pharm. Bull. 1977, 25, 321-326.
160. Marsden, R.; MacLean, D. B. Can. J. Chem. 1984, 62, 306-308.
161. Ibragimova, M. U.; Yunusov, M. S.; Yu, S. Khim. Prirodu. Soedin. 1970, 438-440; Chem. Abstr. 1971, 74, 54046r.
162. Ibragimova, M. U.; Yunusov, M. S.; Yu, S. Khim. Prirodu. Soedin. 1970, 438-440; Chem. Abstr. 1971, 74, 54046r.
163. Margvelashvili, N. N.; Kirjanova, A. T.; Tolkachev, O. N. Khim. Prirodu. Soedin. 1972, 127-128; Chem. Abstr. 1972, 77, 58825d.
164. Margvelashvili, N. N.; Kirjanova, A. T.; Tolkachev, O. N. Khim. Prirodu. Soedin. 1972, 127-128; Chem. Abstr. 1972, 77, 58825d.
165. Shono, T.; Usui, Y.; Mizutani, T.; Hamaguchi, H. Tetrahedron Lett. 1980, 21, 3073-3076.
166. Govindachari, T. R.; Nagarajan, K.; Charubala, R.; Pai, B. R. Ind. J. Chem. 1970, 8, 763-765.
167. Perkin, W. H.; Ray, J. N.; Stauton, J.; Hirst, M. J. Chem. Soc. 1925, 127, 740-744.
168. Dean, R. T.; Rapoport, H. J. Org. Chem. 1978, 43, 2115-2122.
169. Haworth, R. D.; Koepfli, J. B.; Perkin Jr., W. H. J. Chem. Soc. 1927, 548-554.
170. Bradsher, C. K.; Dutta, N. L. J. Org. Chem. 1961, 26, 2231-2234.
171. Kiparisaides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770-2779.
172. Tani, C.; Imanishi, I.; Nishijo, J. Yakugaku Zasshi 1970, 90, 407-411; Chem. Abstr. 1970, 73, 25719m.
173. Tani, C.; Imanishi, I.; Nishijo, J. Yakugaku Zasshi 1970, 90, 407-411; Chem. Abstr. 1970, 73, 25719m.
174. Narasimuhan, N. S.; Ranade, A. C.; Bhide, B. S. Indian J. Chem. 1981, 20B, 439-440.
175. Ninomiya, I., Naito, T.; Takasugi, H. J. Chem. Soc., Perkin Trans 1 1975, 1720-1724.
176. Kametani, T.; Ihara, M. J. Chem. Soc. (C) 1967, 530-532.
177. Lentz, G. R. J. Org. Chem. 1974, 39, 2846-2851.
178. Rajaraman, R.; Pai, B. R.; Premila, M. S.; Suguna, H. Indian J. Chem. 1977, 15B, 876-879.
179. Haworth, R. D.; Perkin, W. H., Jr. J. Chem. Soc. 1926, 1769-1784.
180. Kametani, T.; Noguchi, I.; Saito, K.; Kaneda, S. J. Chem. Soc. (C) 1969, 2036-2038.