Tandem oxidative acetalization-intramolecular Diels-Alder reactions of 2-methoxyphenols. Simple synthesis of bicyclo[2.2.2]octenone derivatives

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 4111-4118

  Chu, Chrong Shyua ^a   Lee, Tsung Ho ^a   Rao, Polisetti Dharma ^a   Song, Ling Duan ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; BICYCLO[2.2.2]OCTENONE DERIVATIVE; METHYL VANILLATE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE IMAGING; ORGANIC CHEMISTRY; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033612309     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990232k     Document Type: Article

References (77)

1. (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
2. (b) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. Natural Products Synthesis Through Pericyclic Reactions; ACS Monograph no. 180; American Chemical Society: Washington, DC, 1983.
3. (c) Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; John-Wiley: New York, 1990.
4. (d) Ho, T.-L. Carbocyclic Ring Construction in Terpene Synthesis; VCH: Weinheim, 1988.
5. (e) Curran, D. P., Ed. Advances in Cycloaddition; JAI Press: Greenwich, 1990; Vols. 1-3.
6. For a recent review on intermolecular Diels-Alder reactions, see: (a) Oppolzer, W. Combining C-C π-bonds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.1.
7. Alder, K.; Schumacher, M. Fortsch. Chem. Org. Naturst. 1953, 10, 66.
8. For some recent reviews on intramolecular Diels-Alder reactions, see: (a) Rough, W. R. Combining C-C π-bonds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.4. (b) Craig, D. Chem. Soc. Rev. 1987, 187. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1.
9. For some recent reviews on intramolecular Diels-Alder reactions, see: (a) Rough, W. R. Combining C-C π-bonds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.4. (b) Craig, D. Chem. Soc. Rev. 1987, 187. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1.
10. For some recent reviews on intramolecular Diels-Alder reactions, see: (a) Rough, W. R. Combining C-C π-bonds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.4. (b) Craig, D. Chem. Soc. Rev. 1987, 187. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1.
11. For some recent reviews on intramolecular Diels-Alder reactions, see: (a) Rough, W. R. Combining C-C π-bonds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.4. (b) Craig, D. Chem. Soc. Rev. 1987, 187. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1.
12. (a) Kirby, A. J. Adv. Phy. Org. Chem. 1980, 17, 183.
13. (b) Page, M. I. Chem. Soc. Rev. 1973, 2, 295.
14. Gauthier, D. R.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289.
15. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
16. (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992.
17. (b) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
18. (c) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
19. (d) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195.
20. (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1903, 32, 131.
21. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
22. (a) Wender, P. A.; Miller, B. L. Towards the Ideal Synthesis: Connectivity Analysis and Multibond-forming Processes. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, 1993; Vol. 2, pp 27-66.
23. (b) Hudlicky, T. Chem. Rev. 1996, 96, 3.
24. (a) Neuschutz, K.; Velker, J.; Neier, R. Synthesis 1998, 227.
25. (b) Winkler, J. D. Chem. Rev. 1996, 96, 167.
26. (a) Chu, C.-S. Lee, T.-H., Liao, C.-C. Synlett 1994, 635.
27. (b) Chen, C.-H.; Rao, P. D.; Liao, C.-C. J. Am. Chem. Soc. 1998, 120, 13254.
28. (a) Mitchell, A. S.; Russell, R. A. Tetrahedron. Lett. 1993, 34, 545.
29. (b) Tamura, Y.; Yakura, T.; Harnata, J. I.; Kita, Y. J. Org. Chem. 1987, 52, 3927.
30. (c) Yahura, T.; Tohma, H.; Kikchi, K.; Kita, Y. Synthesis 1989, 126.
31. (a) Andersson, G.; Berntsson, P. Acta Chem. Scand. B 1975, 29, 948.
32. (b) Andersson, G. Acta Chem. Scand. B 1976, 30, 64.
33. (c) Andersson, G. Acta Chem. Scand. B 1976, 30, 403.
34. Chu, C.-S.; Liao, C.-C.; Rao, P. D. Chem. Commun. 1996, 1537.
35. Uyehara, T.; Osanai, K.; Sugimoto, M.; Suzuki, I.; Yamamoto, M. J. Am. Chem. Soc. 1989, 111, 7264.
36. (a) Givens, R. S.; Oettle, W. F.; Coffin, R. L.; Carlson, R. G. J. Am. Chem. Soc. 1971, 93, 3957.
37. (b) Demuth, M.; Schaffner, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 820.
38. (c) Singh, V.; Porinchu, M. J. Chem. Soc., Chem. Commun. 1993, 134.
39. (a) Zimmerman, H. E.; Armesto, D. Chem. Rev. 1996, 96, 3065.
40. (b) Demuth, M. Org. Photochem. 1991, 11, 37.
41. (a) Hsu, D.-S.; Rao, P. D.; Liao, C.-C. Chem. Commun. 1998, 1795.
42. (b) Singh, V.; Thomas, B. J. Org. Chem. 1997, 62, 5310.
43. (c) Hwang, J.-T.; Liao, C.-C. Tetrahedron Lett. 1991, 32, 6583.
44. Demuth, M.; Hinsken, W. Angew. Chem., Int. Ed. Engl. 1985, 24, 973.
45. (e) Mehta, G.; Subrahmanyam, D. J. Chem. Soc., Perkin Trans. 1 1991, 395.
46. (a) Lee, T.-H.; Liao, C.-C.; Liu, W.-C. Tetrahedron Lett. 1996, 37, 6819.
47. (b) Hsu, P.-Y.; Lee, Y.-C.; Liao, C.-C. Tetrahedron Lett. 1998, 39, 659.
48. (a) Bhamare, N. K.; Granger, T.; John, C. R.; Yates, P. Tetrahedron Lett. 1991, 32, 4439.
49. (b) Bhamare, N. K.; Granger, T.; John, C. R.; Yates, P. J. Chem. Soc., Chem. Commun. 1990, 739.
50. (c) Yates, P.; Macas, T. S.; Can. J. Chem. 1988, 66, 1.
51. Schultz, A. G.; Lavieri, F. P.; Snead, T. S. J. Org. Chem. 1985, 50, 3086.
52. (a) Frater, G.; Wenger, J. Helv. Chim. Acta 1984, 67, 1702.
53. (b) Greuter, H.; Schmidt, H.; Frater, G. Helv. Chim. Acta 1977, 60, 1701.
54. (c) Frater, G. Helv. Chim. Acta 1974, 57, 172.
55. (d) Greuter, H.; Frater, G.; Schmidt, H. Helv. Chim. Acta 1972, 55, 526.
56. (e) Greuter, H.; Schmidt, H. Helv. Chim. Acta 1972, 55, 2382.
57. (a) Fukamiya, N.; Kato, M.; Yoshikoshi, A. J. Chem. Soc., Chem. Commun. 1971, 1120.
58. (b) Fukamiya, N.; Kato, M.; Yoshikoshi, A. J. Chem. Soc., Perkin Trans. 1 1973, 1843.
59. (a) Broke, J. M.; Hall, D. H.; Shearer, H. M. M. J. Chem. Soc., Perkin Trans. 1 1976, 780.
60. (b) Broke, J. M.; Hall, D. H. J. Chem. Soc., Perkin Trans. 1 1976, 1463.
61. (c) Broke, J. M. J. Chem. Soc., Perkin Trans. 1 1974, 233.
62. (a) Bichman, D. J.; Yates, P. J. Am. Chem. Soc. 1972, 94, 4773.
63. (b) Bichman, D. J.; Yates, P. Can. J. Chem. 1975, 53, 2054.
64. (c) Yates, P.; Auksi, H. J. Chem. Soc., Chem. Commun. 1976, 1016.
65. (d) Yates, P.; Auksi, H. Can. J. Chem. 1979, 57, 2853.
66. 27b
67. (b) Shen, Y.-L. Master Degree Thesis, National Tsing Hua University, Hsinchu, Taiwan, 1995.
68. Lee, T.-H.; Liao, C.-C. Tetrahedron Lett. 1996, 37, 6869.
69. Liu, W.-C.; Liao, C.-C. Chem. Commun. 1998, 117.
70. (a) Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 2596.
71. (b) Imamoto, T.; Oho, M. Chem. Lett. 1987, 501.
72. (a) Liao, C.-C.; Wei, C.-P. Tetrahedron Lett. 1989, 30, 2255.
73. (c) Liu, W.-C.; Liao, C.-C. Synlett 1998, 912.
74. (d) Hsiesh, M.-F.; Liao, C.-C. Unpublished results.
75. Lee, T.-H., Rao, P. D.; Liao, C.-C. Chem. Commun. 1999, in press.
76. (a) Hsiu, P.-Y.; Liao, C.-C. Chem. Commun. 1997, 1086.
77. (b) Carlini, R.; Higgs, K.; Rodrigo, R.; Taylor, N. Chem. Commun. 1998, 65.