Spiroepoxycyclohexa-2,4-dienones in organic synthesis

Accounts of Chemical Research

Volumn 32, Issue 4, 1999, Pages 324-333

  Singh, Vishwakarma ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; SPIRO COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; PHOTOCHEMISTRY; SYNTHESIS;

EID: 0032911430     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar970350z     Document Type: Article

References (104)

1. (a) Waring, A. J. In Advances in Alicyclic Chemistry; Hart, H., Karabatsos, G. J., Eds.; Academic Press: New York, 1966; Vol. 1, pp 129-256 and references therein.
2. (a) Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850-3866.
3. (a) Corey, E. J.; Dittami, J. P. J. Am. Chem. Soc. 1985, 107, 256-257.
4. (b) Quinkert, G. In Organic Synthesis; Streith, J., Prinzbach, H., Schill, G., Eds.; Backwell Scientific Publication: Oxford, 1985, pp 131-143.
5. (a) Singh, V.; Thomas, B. J. Chem. Soc., Chem. Commun. 1992, 1211-1213.
6. (b) Singh, V.; Porinchu, M. J. Chem. Soc., Chem. Commun. 1993, 134-136.
7. (c) Singh, V.; Porinchu, M. Tetrahedron Lett. 1993, 34, 2817-2820.
8. (a) Singh, V.; Prathap, S. Synlett 1994, 542-544.
9. (b) Singh, V.; Thomas, B.; Sharma, U. Tetrahedron Lett. 1995, 36, 3421-3424.
10. (c) Singh, V.; Porinchu, M. Tetrahedron 1996, 52, 7087-7126.
11. (d) Singh, V.; Thomas, B. J. Org. Chem. 1997, 62, 5310-5320.
12. (e) Singh, V.; Sharma U. J. Chem. Soc., Perkin Trans I 1998, 305-312.
13. (a) Mehta, G.; Srikrishna, A. Chem Rev. 1997, 97, 671-719.
14. (b) Singh, V.; Thomas, B. Tetrahedron Rep. 1998, 54, 3647-3692.
15. (c) Jung, M. E.; Rayle, H. L. J. Org. Chem. 1997, 62, 4601-4609.
16. (d) Tormo, J.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4851-4856.
17. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry, Hafner, L.; Rees, C. W.; Trost, B. M., Lehn, J. M., Schleyer, P. v. R., Zaharadnik, R., Eds.; Springer-Verlag: New York, 1987, Vol. 26, 1-225 and references therein.
18. (a) Curtin, D. Y.; Dybvig, D. H. J. Am. Chem. Soc. 1962, 84, 225-232.
19. (b) Miller, B. J. Am. Chem. Soc. 1965, 87, 5115-5120.
20. (c) Miller, B. J. Org. Chem. 1970, 35, 4262-4264.
21. Alder, K.; Floch, H. F.; Lessenich A. Chem. Ber. 1957, 90, 1709-1720.
22. Schultz, A. G.; Dittami, J. P.; Lavieri, F. P.; Salowey, C.; Sundararaman, P.; Szymula, M. B. J. Org. Chem. 1984, 49, 4429-4440.
23. (a) Adler, E.; Brasen, S.; Miyake, H. Acta Chem. Scand. 1971, 25, 2055-2069.
24. (b) Adler, E.; Holmberg, K. Acta Chem. Scand. 1974, 28B, 465-472.
25. (a) Singh, V. K.; Raju, B. N. S.; Deota, P. T. Synth. Commun. 1986, 16, 17-31.
26. (b) Makosza, M. Pol. Pat. 1968, 55731. (Chem. Abstr. 1969, 70, 106047).
27. (b) Makosza, M. Pol. Pat. 1968, 55731. (Chem. Abstr. 1969, 70, 106047).
28. Stone, K. J.; Little, R. D. J. Org. Chem. 1984, 49, 1849-1853.
29. Corey, E. J. and Cheng, X. M. The Logic of Chemical Synthesis; John Wiley & Sons: New York, 1989.
30. (a) Sauer, J.; Angew. Chem., Int. Ed. Engl. 1967, 6, 16-33.
31. (b) Sauer, J. Angew. Chem. Int. Ed. Engl. 1966, 5, 211-230.
32. (a) Woodward, R. B.; Hoffman, R. Conservation of Orbital Symmetry; Academic Press: New York, 1972; pp 65-113.
33. (b) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: Chichester, 1978; Chapter 4, pp 86-181.
34. (a) Bartby, D. M.; Fray, G. I. J. Chem. Soc. (C), 1971, 970-974.
35. (b) Bartby, D. M.; Chadwick, J. C.; Fray, G. I.; Saxton, R. G. Tetrahedron, 1977, 33, 1527-1532.
36. (c) Gesson, J.-P.; Hervaud, L.; Mondon, M. Tetrahedron Lett. 1993, 34, 2941-2944.
37. Singh, V.; Sharma, U.; Prasanna, V.; Porinchu, M. Tetrahedron 1995, 51, 6015-6032.
38. (a) Singh, V.; Deota, P. T.; Bedekar, A. V. J. Chem. Soc., Perkin Trans. 1, 1992, 903-912.
39. (b) Singh, V. K.; Deota, P. T. J. Chem. Res. (S) 1989, 390-391.
40. Fry, A. J. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: New York, 1991; Vol. 8, pp 983-997.
41. (a) Bowden, K.; Heilborn, H.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39-45.
42. (b) Harrison, I. T.; Harrison, S. Compendium of Organic Synthetic Methods; Wiley-Interscience: New York, 1971.
43. House, H. O. Modern Synthetic Reactions; The Benjamin/Cummings Publishing Co.: Menlo Park, CA 1972; pp 492-519.
44. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; John Wiely & Sons: NewYork, 1967; pp 992-1000.
45. (a) Schuster, D. I. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, pp 232-279.
46. (b) Houk, K. N. Chem. Rev. 1976, 76, 1-74.
47. (c) Dauben, W. G.; Lodder, G.; Ipaktschi, J. Top. Curr. Chem. 1974, 54, 73-114.
48. (d) Hixson, S. S.; Mariano, P. S.; Zimmerman, H. E. Chem. Rev. 1973, 73, 531-551.
49. (a) Zimmerman, H. E.; Armesto, D. Chem. Rev. 1996, 96, 3065-3112.
50. (b) Demuth, M. In Organic Photochemistry, Padwa, Ed.; Marcel Dekker: New York, 1991; Vol. 11, pp 37-97 and references therein.
51. (a) Singh, V. K.; Deota, P. T.; Raju, B. N. S. Synth. Commun. 1987, 17, 115-124.
52. (b) Singh, V. K.; Raju, B. N. S.; Deota, P. T. Indian J. Chem. 1987, 26B, 301-304.
53. Singh, V. K.; Raju, B. N. S. Synth. Commun. 1988, 18, 1513-1524.
54. (a) Henne, A.; Siew, N. P. Y.; Schaffner, K. J. Am. Chem. Soc. 1979, 101, 3671-3673.
55. (b) Mirbach, M. J.; Henne A.; Schaffner, K. J. Am. Chem. Soc. 1978, 100, 7127-7128.
56. (a) Givens,. R. S.; Chae, W. K.; Matuszewski, B. J. Am. Chem. Soc. 1982, 104, 2456-2466.
57. (b) Coffin, R. L.; Cox, W. W.; Carlson, R. G.; Givens, R. S. J. Am. Chem. Soc. 1979, 101, 3261-3272.
58. (c) Givens, R. S.; Oettle, W. F.; Coffin, R. L.; Carlson, R. G. J. Am. Chem. Soc. 1971, 93, 3957-3962.
59. (a) Schuster, D. I.; Calcaterra, L. T. J. Am. Chem. Soc. 1981, 103, 2460-2461.
60. (b) Schuster, D. I.; Eriksen, J.; Engel, P. S.; Shexnayder, M. A. J. Am. Chem. Soc. 1976, 98, 5025-5027.
61. (c) Dauben, W. G.; Lodder, G.; Robbins, J. D. J. Am. Chem. Soc. 1976, 98, 3030-3031.
62. (d) Houk, K. N.; Northington, D. J.; Duke, R. E., Jr. J. Am. Chem. Soc. 1972, 94, 6233-6235.
63. Wilsey, S.; Bearpark, M. J.; Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1996, 118, 176-184.
64. (a) Engel, P. S.; Schexnayder, M. A. J. Am. Chem. Soc. 1972, 94, 4357-4359.
65. (b) Cargill, R. L.; King, T. Y.; Sears, A. B.; Willcott, M. R. J. Org. Chem. 1971, 36, 1423-1428.
66. Zimmerman, H. E.; Pratt, A. C. J. Am. Chem. Soc. 1970, 92, 1409.
67. (a) Parker, S. D.; Rogers, N. A. J. Tetrahedron Lett. 1976, 4389-4392.
68. (b) Eckersley, T. J.; Parker, S. D.; Rogers, N. A. J. Tetrahedron 1984, 40, 3749-3758.
69. (a) Singh, V.; Prathap, S.; Porinchu, M. J. Org. Chem. 1998, 63, 4011-4017.
70. (b) Singh, V.; Prathap, S.; Porinchu, M. Tetrahedron Lett. 1997, 38, 2911-2914.
71. (c) Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108-7116,
72. (d) Tanaka, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1996, 1839-1840,
73. (e) Balme, G.; Bouyssi, D. Tetrahedron 1994, 50, 403-414 and references therein.
74. (a) Ihara, M.; Suzuki, T.; Katogi, M.; Taniguchi, N.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1991, 646-647.
75. (b) Meyers, A. I.; Bienz, S. J. Org. Chem. 1990, 55, 791-798.
76. (c) Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990, 55, 4504-4506.
77. (d) Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 928-932. For other syntheses of capnellene, see ref 6a.
78. Funk, R. L.; Bolton; G. L.; Daggett, J. U.; Hansen, M. M.; Horcher, L. H. M. Tetrahedron 1985, 41, 3479-3495.
79. (a) Mulzer, J. In Organic Synthesis Highlights; Mulzer, J., Altenbach, H.-J., Braun, M., Krohn, K., Reissig, H.-U., Eds.; VCH Publishers, Inc: New York, 1991, pp 323-334 and references therein.
80. (b) Singh, V.; Samanta, B. Unpublished results.
81. Singh, V.; Prathap, S. Tetrahedron 1996, 52, 14287-14296.
82. Tsuji, J.; Shimizu, I.; Yamamoto, K. Tetrahedron Lett. 1976, 2975-2976.
83. (a) Arnone, A.; Brambilla, U.; Nasini, G.; Vajna dePava, O. Tetrahedron 1995, 51, 13357-13364.
84. (b) Arnone, A.; Nasini, G.; Vajna dePava, O.; Assante, G. J. Chem. Soc., Perkin Trans. I, 1992, 615-620.
85. (c) Donnelly, D. M. X.; Hutchinson, R. M.; Coveney, D.; Yonemitsu, M. Phytochemistry 1990, 29, 2569-2572.
86. (a) Johnson, E. P.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1991, 113, 381-382. and references therein.
87. (b) Oppolzer, W.; Nakao, A. Tetrahedron Lett. 1986, 5471-5474.
88. (c) Semmelhack, M. F. In Strategies and Tactics in Organic Synthesis; Lindberg, T., Ed.; Academic Press: New York, 1984; pp 201-222.
89. (a) Ayer, W. A.; Browne, L. M. Tetrahedron 1981, 37, 2199-2248.
90. (b) Ayer, W. A.; Nakashima, T. T.; Saeedi-Ghomi, M. H. Can. J. Chem. 1984, 62, 531-533.
91. (c) Shirahama, H.; Osawa, E.; Matsumoto, T. J. Am. Chem. Soc. 1980, 102, 3208-3213.
92. (d) Morisaki, N.; Furukawa, J.; Kobayashi, H.; Iwasaki, S.; Nozoe, S.; Okuda, S. Tetrahedron Lett. 1985, 4755-4758.
93. (e) Hayano, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. Helv. Chim. Acta, 1981, 64, 1347-1364.
94. Paquette, L. A. In Strategies and Tactics of Organic Synthesis; Lindberg, T., Ed.; Academic Press: New York, 1984; pp 175-200 and references therein.
95. (a) Mehta, G.; Prabhakar, C.; Nethaji, M.; Venkatesan, K. J. Chem. Soc. Chem. Commun. 1993, 483-485.
96. (b) Marchand, A. P.; Annapurna, P.; Taylor, R. W.; Simmons, D. L.; Watson, W. H.; Nagl, A.; Flippen-Anderson, J. L.; Gilardi, R.; George, C. Tetrahedron 1990, 46, 5077-5084.
97. Alfaro, I.; Ashton, W.; Rabone, K. L.; Rogers, N. A. J. Tetrahedron 1974, 30, 559-569.
98. (a) Singh, V.; Jagadish, B. Tetrahedron 1996, 52, 3693-3704.
99. (b) Singh V.; Jagadish, B. Indian J. Chem. 1997, 36B, 391-393.
100. (a) Taber, D. F. Intramolecular Diels-Alder and Ene Reactions, Springer-Verlag: New York, 1984; pp 1-60.
101. (b) Schultz, A. G.; Lavieri, F. P.; Snead, T. E. J. Org. Chem. 1985, 50, 3086-3091.
102. (c) Bhamare, N. K.; Granger, T.; Macas, T. S.; Yates, P. J. Chem. Soc., Chem. Commun. 1990, 739-740.
103. Singh, V.; Alam, S. Q.; Porinchu, M. Tetrahedron 1995, 51, 13423-13434.
104. Singh, V.; Alam, S. Q. Unpublished results.