Introduction of Bicyclic Ketal Chemistry: Synthesis and Transformation Reaction of 6,8-Dioxabicyclo[3.2.1]octane Skeletal System

Synlett

Volumn , Issue 12, 2003, Pages 1759-1777

  Jun, Jong Gab ^a  

^a Hallym University   (South Korea)

Author keywords

6,8 dioxabicyclo 3.2.1 octane; Bicyclic ketal; C O bond cleavage; Lewis acid; One pot transformation

Indexed keywords

6,8 DIOXABICYCLO[3.2.1]OCTANE; ACETAL; ETHER DERIVATIVE; KETONE DERIVATIVE; OCTANE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0142123975     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41415     Document Type: Article

References (136)

1. (a) Francke, W.; Schroder, W. Curr. Org. Chem. 1999, 3, 407; and references cited therein.
2. (b) Francke, W.; Schroeder, F.; Philipp, P.; Meyer, H.; Sinnwell, V.; Gries, G. Bioorg. Med. Chem. 1996, 4, 363.
3. (a) Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, E.; Zheng, S.; Chen, H. J. Am. Chem. Soc. 1995, 117, 1155.
4. (b) Moore, R. E.; Scheuer, P. Science 1971, 172, 495.
5. (a) Ogasawara, K. Yuki Gosei Kagaku Kyokaishi 2002, 60, 316; Chem. Abstr. 2002, 137: 295150.
6. (a) Ogasawara, K. Yuki Gosei Kagaku Kyokaishi 2002, 60, 316; Chem. Abstr. 2002, 137: 295150.
7. (b) Kadota, K.; Kurusu, T.; Taniguchi, T.; Ogasawara, K. Adv. Synth. Catal. 2001, 343, 618.
8. (c) Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Synthesis 1999, 341.
9. (d) Mori, K. Tetrahedron 1974, 30, 4223.
10. (a) Trzoss, M.; Shao, J.; Bienz, S. Tetrahedron 2002, 58, 5885.
11. (b) Mori, K. Eur. J. Org. Chem. 1998, 1479.
12. (c) Yus, M.; Ramon, D. J. Org. Chem. 1992, 57, 750.
13. (d) Braun, M. Org. Synth. Highlights 1991, 335.
14. (a) Mayer, S. F.; Mang, H.; Steinreiber, A.; Saf, R.; Faber, K. Can. J. Chem. 2002, 80, 362.
15. (b) Gallos, J. K.; Kyradjoglou, L. C.; Koftis, T. V. Heterocycles 2001, 55, 781.
16. (c) Burke, S. D.; Mueller, N.; Beaudry, C. M. Org. Lett. 1999, 1, 1827.
17. (d) Silverstein, R. M.; Brownlee, R. G.; Bellas, T. E.; Wood, D. L.; Browne, L. E. Science 1968, 159, 889.
18. (a) Taniguchi, T.; Ohnishi, H.; Ogasawara, K. Chem. Commun. 1996, 1477.
19. (b) Levoglucosenone and Levoglucosans Chemistry and Applications; Witczak, Z. J., Ed.; ATL Press: Prospect IL, 1994, ; Chem. Abstr. 1994, 122: 188015.
20. (b) Levoglucosenone and Levoglucosans Chemistry and Applications; Witczak, Z. J., Ed.; ATL Press: Prospect IL, 1994, ; Chem. Abstr. 1994, 122: 188015.
21. (c) Witczak, Z. J. Stud. Nat. Prod. Chem. 1994, 14, 267.
22. (d) Gore, W. E.; Pearce, G. T.; Silverstein, R. M. J. Org. Chem. 1976, 41, 603.
23. (a) Steinreiber, A.; Mayer, S. F.; Faber, K. Synthesis 2001, 2035.
24. (b) Nair, V.; Sheela, K. C.; Sethumadhavan, D.; Bindu, S.; Rath, N. P.; Eigendorf, G. K. Synlett 2001, 272.
25. (c) Francisco, C. G.; Herrera, A. J.; Suarez, E. Tetrahedron Lett. 2000, 41, 7869.
26. (d) Machetti, F.; Ferrali, A.; Menchi, G.; Occhiato, E. G.; Guarna, A. Org. Lett. 2000, 2, 3987.
27. (e) Hodgson, D. M.; Villalonga-Barber, C. Tetrahedron Lett. 2000, 41, 5597.
28. (a) Voight, E. A.; Rein, C.; Burke, S. D. Tetrahedron Lett. 2001, 42, 8747.
29. (b) Fujiwara, K.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron 2000, 56, 1065.
30. Lipkowitz, K. B.; Mundy, B. P.; Geeseman, D. Synth. Commun. 1973, 3, 453.
31. Mundy, B. P.; Lipkowitz, K. B.; Dirks, G. W. Synth. Commun. 1975, 5, 7.
32. Jun, J.-G.; Shin, D. G.; Lee, C. K.; Sin, K. S. Bull. Korean Chem. Soc. 1990, 11, 307.
33. Conforth, J. W.; Conforth, R. H.; Mathew, K. K. J. Chem. Soc. 1959, 112.
34. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 9, 2199.
35. Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748.
36. Bartlett, P. A. Tetrahedron 1980, 36, 2.
37. Jun, J.-G.; Shin, D. G. J. Chem. Soc., Perkin Trans. 1 1991, 956.
38. (a) Jun, J.-G.; Shin, D. G.; Shin, H. S. Bull. Korean Chem. Soc. 1992, 13, 98.
39. (b) Bartlett, K. E. Synth. Commun. 1992, 22, 2165.
40. Wood, D. L.; Browne, L. E.; Ewing, B.; Lindahl, K.; Bedard, W. D.; Tilden, P. E.; Mori, K.; Pitman, G. B.; Hughes, P. R. Science 1976, 192, 896.
41. Payne, T. L.; Coster, J. E.; Richerson, J. V.; Edson, L. J.; Hart, E. R. Environ. Entomol. 1978, 7, 78.
42. Wiesler, D. P.; Schwende, F. J.; Carmack, M.; Novotny, M. J. Org. Chem. 1984, 49, 882.
43. Mundy, B. P.; Bornmann, W. G. J. Org. Chem. 1984, 49, 5264.
44. McElvain, S. M.; Clarke, R. L.; Jones, G. D. J. Am. Chem. Soc. 1942, 64, 1966.
45. Noya, Y.; Kotake, M. Tetrahedron Lett. 1967, 8, 2459.
46. (a) Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4093.
47. (b) Alston, P. V.; Shillady, D. D. J. Org. Chem. 1974, 39, 3402.
48. (c) Mundy, B. P.; Lipkowitz, K. B.; Dirks, G. W. Heterocycles 1977, 6, 51.
49. Jun, J.-G.; Lee, D. W. Tetrahedron Lett. 1997, 38, 8207.
50. Jun, J.-G.; Lee, I.-S. Synth. Commun. 2000, 30, 1159.
51. Kinzer, G. W.; Fentiman, A. F.; Page, T. F.; Foltz, R. L.; Vite, J. P.; Pitman, G. B. Nature (London) 1969, 221, 477.
52. Utaka, M.; Makino, H.; Oota, Y.; Tsuboi, S.; Takeda, A. Tetrahedron Lett. 1983, 24, 2567.
53. Nakamura, E.; Murofushi, T.; Shimizu, M.; Kuwajima, I. J. Am. Chem. Soc. 1976, 98, 2346.
54. Johnson, F. Chem. Rev. 1968, 68, 375.
55. House, H. O.; Kramer, V. J. Org. Chem. 1963, 28, 3362.
56. Gorowitz, W. D.; Joseph, M. A. J. Org. Chem. 1967, 32, 3289.
57. Lipkowitz, K. B. Ph.D. Dissertation; Montana State University Bozeman: USA, 1975, 27-36.
58. Jun, J.-G.; Kim, S. S. Bull. Korean Chem. Soc. 1994, 15, 612.
59. Zaugg, H. E. J. Am. Chem. Soc. 1961, 83, 837.
60. Williard, P. G.; Carpenter, G. B. J. Am. Chem. Soc. 1986, 108, 462.
61. (a) Chong, B.-D.; Ji, Y.-I.; Oh, S.-S.; Yang, J.-D.; Baik, W.; Koo, S. J. Org. Chem. 1997, 62, 323.
62. (b) Chen, Y. L.; Mariano, P. S.; Little, G. M.; O'Brien, D.; Huesmann, P. L. J. Org. Chem. 1981, 46, 4643.
63. Jun, J.-G. Bull. Korean Chem. Soc. 1993, 14, 324.
64. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds; Wiley: New York, 1981.
65. Mundy, B. P.; Bjorklund, M. Tetrahedron Lett. 1985, 26, 3899.
66. Buchi, G.; Powell, Jr.; J, E. J. Am. Chem. Soc. 1970, 92, 3126.
67. Baldwin, J. E.; Hofle, G. A.; Lever, O. W. J. Am. Chem. Soc. 1974, 96, 7125.
68. Evans, D. A.; Andrews, G. C.; Buckwalter, B. J. Am. Chem. Soc. 1974, 96, 5560.
69. Still, W. C.; MacDonald, T. L. J. Am. Chem. Soc. 1974, 96, 5561.
70. Riobe, O.; Lebouc, A.; Delaunay, J. C. R. Acad. Sci. 1977, 284, 281.
71. (a) Bates, R. B.; Kroposki, L. M.; Potter, D. E. J. Org. Chem. 1972, 37, 560.
72. (b) Settle, F. A.; Hagerty, M.; Eastham, J. F. J. Am. Chem. Soc. 1964, 86, 2076.
73. Undesirable side products and non-homogeneous systems could be avoided by dilution with THF to 0.1-1.0 M, the anions were stable in THF once formed.
74. Jun, J.-G.; Chun, H. S.; Lee, D. W. Bull. Korean Chem. Soc. 1996, 17, 980.
75. (a) Srivastava, R. M.; Pavao, A. C.; Seabra, G. M.; Brown, R. K. J. Mol. Struct. 1997, 412, 51.
76. (b) Bjorklund, M.; Jun, J.-G.; Mundy, B. P. Tetrahedron Lett. 1985, 26, 3895.
77. Daterman, G. E.; Peterson, L. J.; Robbins, R. G.; Sower, L. L.; Daves, G. D. Jr.; Smith, R. G. Environ. Entomol. 1976, 5, 1187.
78. Dauben, W. G.; Dietsche, T. J. J. Org. Chem. 1972, 37, 1212.
79. Doering, W. von E.; Roth, W. R. Tetrahedron 1962, 18, 67.
80. Buchi, G.; Powell, J. E. Jr. J. Am. Chem. Soc. 1970, 92, 3126.
81. Black, D. S.; Wade, A. M. J. Chem. Soc., Chem. Commun. 1970, 871.
82. Ha, T. H.; Jun, J.-G. Bull. Korean Chem. Soc. 1996, 17, 112.
83. Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 18, 3417.
84. Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249; and references cited therein.
85. Mundy, B. P.; Dirks, G. W.; Larter, A. C.; Lipkowitz, K. B.; Carter, J. J. Org. Chem. 1981, 46, 4005.
86. Jun, J.-G.; Lee, D. W.; Mundy, B. P. Synth. Commun. 1998, 28, 2499.
87. Goldsmith, D. J.; Kennedy, E.; Campbell, R. G. J. Org. Chem. 1975, 40, 3571.
88. (a) Bartlett, K. E.; Fitzgerald, A.; Larsen, R. D.; Rees, M. S.; Mundy, B. P.; Emerson, K. J. Org. Chem. 1991, 56, 1958.
89. (b) Mundy, B. P.; Dirks, G. W.; Larsen, R. D.; Caughlan, C. N. J. Org. Chem. 1978, 43, 2347.
90. Lee, D. W.; Lee, K.-J.; Chi, D. Y.; Jun, J.-G. Bull. Korean Chem. Soc. 1999, 20, 373.
91. Westheimer, F. H.; Nicolaides, N. J. Am. Chem. Soc. 1949, 71, 25.
92. Price, C. C.; Carmelite, D. D. J. Am. Chem. Soc. 1966, 88, 4039.
93. Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol. 7.
94. Jun, J.-G.; Lee, D. W. Synth. Commun. 2000, 30, 73.
95. (a) Gross, R. S.; Watt, D. S. Synth. Commun. 1987, 17, 1749.
96. (b) Fraga, B. M.; Cabrera, I.; Garcia, V. P.; Guillermo, R.; Perales, A. Tetrahedron 1997, 53, 16177.
97. Kim, S.-M.; Maeng, Y. H.; Jun, J.-G. Bull. Korean Chem. Soc. 2002, 23, 154.
98. Grieco, P. A. J. Am. Chem. Soc. 1969, 91, 5660.
99. Jun, J.-G.; Mundy, B. P. Bull. Korean Chem. Soc. 1988, 9, 135.
100. Kim, A.-R.; Lee, I.-S.; Jun, J.-G. Synth. Commun. 2001, 31, 853.
101. Mori, A.; Ishihara, K.; Yamamoto, H. Tetrahedron Lett. 1986, 27, 987.
102. Takano, S.; Akiyama, M.; Ogasawara, K. Chem. Pharm. Bull. 1984, 32, 791.
103. Wakefield, B. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon: Oxford, 1982, Vol. 7.
104. Zweifel, G.; Horng, A.; Plamondon, J. E. J. Am. Chem. Soc. 1974, 96, 316.
105. Greene, T. W. Protective Groups in Organic Synthesis; Wiley: New York, 1981, 116.
106. Bonner, T. G.; Lewis, D.; Rutter, K. J. Chem. Soc., Perkin Trans. 1 1981, 1807.
107. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1979, 20, 4679.
108. Gevorgyan, V.; Liu, J.-X.; Yamamoto, Y. Chem. Commun. 1998, 37.
109. Alzeer, J.; Cai, C.; Vasella, A. Helv. Chim. Acta 1995, 78, 242.
110. Qin, Z.; Cai, M.; Li, Z. Youji Huaxue 2001, 21, 214; Chem. Abstr. 2001, 134: 367088.
111. Qin, Z.; Cai, M.; Li, Z. Youji Huaxue 2001, 21, 214; Chem. Abstr. 2001, 134: 367088.
112. Nutaitis, C. F.; Greshock, T. J.; Houghton, S. R.; Moran, L. N.; Walter, M. A. Org. Prep. Proced. Int. 2002, 34, 332.
113. Kotsuki, H.; Ushio, Y.; Yoshimura, N.; Ochi, M. J. Org. Chem. 1987, 52, 2594.
114. Rolf, D.; Gray, G. R. J. Am. Chem. Soc. 1982, 104, 3539.
115. Mundy, B. P.; Kim, Y. J. Org. Chem. 1982, 47, 3556.
116. Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44.
117. Diner, U. E.; Brown, R. K. Can. J. Chem. 1967, 45, 2547.
118. Jun, J.-G. J. Heterocycl. Chem. 1997, 34, 633.
119. Mori, A.; Ishihara, K.; Arai, I.; Yamamoto, H. Tetrahedron 1987, 43, 755.
120. Jun, J.-G.; Suh, S.; Shin, D. G. J. Chem. Soc., Perkin Trans. 1 1989, 1349.
121. Jun, J.-G.; Shin, H. S.; Kim, S. H. J. Chem. Soc., Perkin Trans. 1 1993, 1815.
122. Jun, J.-G.; Shin, H. S. Synth. Commun. 1993, 23, 1871.
123. Corey, E. J.; Danheiser, R. L.; Chandrasekaran, S. J. Org. Chem. 1976, 41, 260.
124. Morris, J.; Wishka, D. G. Tetrahedron Lett. 1988, 29, 143.
125. Jun, J.-G.; Ha, T. H.; Mundy, B. P.; Bartlett, K. E.; Bain, R. S.; Cardellina, J. H. II. J. Chem. Soc., Perkin Trans. 1 1994, 2643.
126. Jun, J.-G.; Gray, G. R. Carbohydr. Res. 1987, 163, 247.
127. Jun, J.-G.; Ha, T. H.; Kim, D.-W. Tetrahedron Lett. 1994, 35, 1235.
128. Jun, J.-G.; Ha, T. H. J. Heterocycl. Chem. 1997, 34, 325.
129. Nagaoka, M.; Nagasawa, E.; Sato, S.; Numazawa, M. Chem. Pharm. Bull. 1999, 47, 548.
130. Morita, T.; Okamoto, Y.; Sakurai, H. Tetrahedron Lett. 1978, 19, 2523.
131. Bhatt, M. V.; Babu, J. R. Tetrahedron Lett. 1984, 25, 3497.
132. (a) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426.
133. (b) Oh, J. Tetrahedron Lett. 1997, 38, 3249.
134. Snider, B. B.; Johnston, M. I. Tetrahedron Lett. 1985, 26, 5497.
135. McElvain, S. M.; Clarke, R. L.; Jones, G. D. J. Am. Chem. Soc. 1942, 64, 1966.
136. Jun, J. G.; Kim, A.-R.; Kim, S. H. Synth. Commun. 2002, 32, 45.