Photochemical rearrangements of quinone monoketals

Tetrahedron

Volumn 52, Issue 16, 1996, Pages 5707-5738

  Pirrung, Michael C ^a   Nunn, David S ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; QUINONE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; PHOTOCHEMISTRY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0029886434     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00207-4     Document Type: Article

References (102)

1. (a) Kahler Arch. Apoth.-Ver. Noerd. Teutschl. 1830, 34, 318-319.
2. (b) Alms, A. Arch. Apoth.-Ver. Noerd. Teutschl. 1830, 34, 319-320.
3. (c) Kahler Arch. Apoth.-Ver. Noerd. Teutschl. 1830, 35, 216-218.
4. (d) Oberdörffer Arch. Apoth.-Ver. Noerd. Teutschl. 1830, 35, 219-223.
5. (e) Alms, A. Arch. Apoth.-Ver. Noerd. Teutschl. 1831, 39, 190-196.
6. (f) Trommsdorff, H. Ann. Pharm. 1834, 11, 190-208.
7. Simonsen, J.; Barton, D. H. R. The Terpenes, University: Cambridge, 1952; Vol. III, Ed. 2, pp 292-295.
8. Cyclohexadienone photochemistry has been the subject of numerous reviews: Schaffner, K.; Demuth, M. In Rearrangements in Ground and Excited States; Mayo, P. d., Ed.; Organic Chemistry Monographs; Academic: New York, 1980; Vol 42, part 3, essay 18.
9. Cyclohexadienone photochemistry has been the subject of numerous reviews: Schaffner, K.; Demuth, M. In Rearrangements in Ground and Excited States; Mayo, P. d., Ed.; Organic Chemistry Monographs; Academic: New York, 1980; Vol 42, part 3, essay 18.
10. For other reviews, see: (a) Schuster, D. I. Acc. Chem. Res. 1978, 11, 65-73.
11. (b) Kropp, P. Org. Photochem. 1967, 1, 1-90.
12. (c) Schaffner, K. Adv. Photochem. 1966, 4, 81-112.
13. (d) Chapman, O. L. Adv. Photochem. 1963, 1, 330-344.
14. (e) Zimmerman, H. E. Adv. Photochem. 1963, 1, 183-208.
15. (f) Caine, D. in "CRC Handbook of Organic Photochemistry and Photobiology," W. M. Horspool and P.-S. Song, Eds., CRC Press, Boca Raton, 1994, p. 701-715
16. Büchi, G.; Kauffman, J. M.; Loewenthal, H. J. E. J. Am. Chem. Soc. 1966, 88, 3403-3408. Marshall, J. A.; Johnson, P. C. J. Org. Chem. 1970, 35, 192-196. Caine, D.; Ingwalson, P. F. J. Org. Chem. 1972, 37, 3751-3752. Caine, D.; Gupton, J. T., III J. Org. Chem. 1975, 40, 809-810. Caine, D.; Frobese, A. S. Tetrahedron Lett. 1977, 3107-3110. Caine, D.; Deutsch, H. J. Am. Chem. Soc. 1978, 100, 8030-8031. Caine, D.; Chu, C.-Y.; Graham, S. L. J. Org. Chem. 1980, 45, 3790-3797.
17. Büchi, G.; Kauffman, J. M.; Loewenthal, H. J. E. J. Am. Chem. Soc. 1966, 88, 3403-3408. Marshall, J. A.; Johnson, P. C. J. Org. Chem. 1970, 35, 192-196. Caine, D.; Ingwalson, P. F. J. Org. Chem. 1972, 37, 3751-3752. Caine, D.; Gupton, J. T., III J. Org. Chem. 1975, 40, 809-810. Caine, D.; Frobese, A. S. Tetrahedron Lett. 1977, 3107-3110. Caine, D.; Deutsch, H. J. Am. Chem. Soc. 1978, 100, 8030-8031. Caine, D.; Chu, C.-Y.; Graham, S. L. J. Org. Chem. 1980, 45, 3790-3797.
18. Büchi, G.; Kauffman, J. M.; Loewenthal, H. J. E. J. Am. Chem. Soc. 1966, 88, 3403-3408. Marshall, J. A.; Johnson, P. C. J. Org. Chem. 1970, 35, 192-196. Caine, D.; Ingwalson, P. F. J. Org. Chem. 1972, 37, 3751-3752. Caine, D.; Gupton, J. T., III J. Org. Chem. 1975, 40, 809-810. Caine, D.; Frobese, A. S. Tetrahedron Lett. 1977, 3107-3110. Caine, D.; Deutsch, H. J. Am. Chem. Soc. 1978, 100, 8030-8031. Caine, D.; Chu, C.-Y.; Graham, S. L. J. Org. Chem. 1980, 45, 3790-3797.
19. Büchi, G.; Kauffman, J. M.; Loewenthal, H. J. E. J. Am. Chem. Soc. 1966, 88, 3403-3408. Marshall, J. A.; Johnson, P. C. J. Org. Chem. 1970, 35, 192-196. Caine, D.; Ingwalson, P. F. J. Org. Chem. 1972, 37, 3751-3752. Caine, D.; Gupton, J. T., III J. Org. Chem. 1975, 40, 809-810. Caine, D.; Frobese, A. S. Tetrahedron Lett. 1977, 3107-3110. Caine, D.; Deutsch, H. J. Am. Chem. Soc. 1978, 100, 8030-8031. Caine, D.; Chu, C.-Y.; Graham, S. L. J. Org. Chem. 1980, 45, 3790-3797.
20. Büchi, G.; Kauffman, J. M.; Loewenthal, H. J. E. J. Am. Chem. Soc. 1966, 88, 3403-3408. Marshall, J. A.; Johnson, P. C. J. Org. Chem. 1970, 35, 192-196. Caine, D.; Ingwalson, P. F. J. Org. Chem. 1972, 37, 3751-3752. Caine, D.; Gupton, J. T., III J. Org. Chem. 1975, 40, 809-810. Caine, D.; Frobese, A. S. Tetrahedron Lett. 1977, 3107-3110. Caine, D.; Deutsch, H. J. Am. Chem. Soc. 1978, 100, 8030-8031. Caine, D.; Chu, C.-Y.; Graham, S. L. J. Org. Chem. 1980, 45, 3790-3797.
21. Büchi, G.; Kauffman, J. M.; Loewenthal, H. J. E. J. Am. Chem. Soc. 1966, 88, 3403-3408. Marshall, J. A.; Johnson, P. C. J. Org. Chem. 1970, 35, 192-196. Caine, D.; Ingwalson, P. F. J. Org. Chem. 1972, 37, 3751-3752. Caine, D.; Gupton, J. T., III J. Org. Chem. 1975, 40, 809-810. Caine, D.; Frobese, A. S. Tetrahedron Lett. 1977, 3107-3110. Caine, D.; Deutsch, H. J. Am. Chem. Soc. 1978, 100, 8030-8031. Caine, D.; Chu, C.-Y.; Graham, S. L. J. Org. Chem. 1980, 45, 3790-3797.
22. Büchi, G.; Kauffman, J. M.; Loewenthal, H. J. E. J. Am. Chem. Soc. 1966, 88, 3403-3408. Marshall, J. A.; Johnson, P. C. J. Org. Chem. 1970, 35, 192-196. Caine, D.; Ingwalson, P. F. J. Org. Chem. 1972, 37, 3751-3752. Caine, D.; Gupton, J. T., III J. Org. Chem. 1975, 40, 809-810. Caine, D.; Frobese, A. S. Tetrahedron Lett. 1977, 3107-3110. Caine, D.; Deutsch, H. J. Am. Chem. Soc. 1978, 100, 8030-8031. Caine, D.; Chu, C.-Y.; Graham, S. L. J. Org. Chem. 1980, 45, 3790-3797.
23. Schultz, A. G.; Lavieri, F. P.; Macielag, M.; Plummer, M. J. Am. Chem. Soc. 1987, 109, 3991-4000. Schultz, A. G.; Lavieri, F. P.; Macielag, M. Tetrahedron Lett. 1986, 27, 1481-1484. Schultz, A. G.; Plummer, M.; Taveras, A. B.; Kullnig, R. K. J. Am. Chem. Soc. 1988, 110, 5547-5555.
24. Schultz, A. G.; Lavieri, F. P.; Macielag, M.; Plummer, M. J. Am. Chem. Soc. 1987, 109, 3991-4000. Schultz, A. G.; Lavieri, F. P.; Macielag, M. Tetrahedron Lett. 1986, 27, 1481-1484. Schultz, A. G.; Plummer, M.; Taveras, A. B.; Kullnig, R. K. J. Am. Chem. Soc. 1988, 110, 5547-5555.
25. Schultz, A. G.; Lavieri, F. P.; Macielag, M.; Plummer, M. J. Am. Chem. Soc. 1987, 109, 3991-4000. Schultz, A. G.; Lavieri, F. P.; Macielag, M. Tetrahedron Lett. 1986, 27, 1481-1484. Schultz, A. G.; Plummer, M.; Taveras, A. B.; Kullnig, R. K. J. Am. Chem. Soc. 1988, 110, 5547-5555.
26. West, F. G.; Fisher, P. V.; Willoughby, C. A. J. Org. Chem. 1990, 55, 5936-5938.
27. For another example of γ-pyranone photochemistry see: Shiozaki, M.; Hiraoka, T. Tetrahedron Lett. 1972, 4655-4658.
28. Koch, T. H.; Soderquist, J. A.; Kinstle, T. H. J. Am. Chem. Soc. 1974, 96, 5576-5578.
29. Taveras, A. G., Jr. Tetrahedron Lett. 1988, 29, 1103-1106.
30. Hewitt, D. G.; Taylor, R. F. J. Chem. Soc., Chem. Commun. 1972, 493-494.
31. Margaretha, P. Helv. Chim. Acta 1976, 59, 661-664.
32. Feldman, K. Ph.D. Thesis, Stanford University, 1984.
33. Liao, C.-C.; Wei, C.-P. Tetrahedron Lett. 1991, 32, 4553-4556.
34. Pirrung, M. C.; Nunn, D. S. Tetrahedron Lett. 1988, 29, 163 .
35. In keeping with the current literature, the term ketal is used throughout this paper, although Chemical Abstracts and IUPAC rules now favor the term acetal for such structures. In this work the terms quinone ketal and quinone monoketal are used interchangeably to refer to 4,4-dialkoxy-2,5-cyclohexadien-1-ones.
36. Swenton, J. S. Chemistry of quinone bis-and monoketals. In The Chemistry of Quinonoid Compounds Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1988; Vol. II, Chapter 15.
37. Aldrich Chemical Co.
38. Sakaino, M. Ph.D. Thesis, Cornell University, 1986.
39. See also: Sakaino, M.; Meinwald, J. Tetrahedron Lett. 1987, 28, 3201-3204.
40. Henton, D. R.; Anderson, K.; Manning, F. M. J.; Swenton, J. S. J. Org. Chem. 1980, 45, 3422-3433.
41. Yoshino, T.; Inaba, S.; Ishido, Y. Bull. Chem. Soc. Jpn. 1973, 46, 553-556.
42. (a) Heller, J. E.; Dreiding, A. S.; O'Connor, B. R.; Simmons, H. E.; Buchanan, G. L.; Raphael, R. A.; Taylor, R. Helv. Chim. Acta 1973, 56, 272-280.
43. (b) Dolson, M. G.; Swenton, J. S. J. Org. Chem. 1981, 46, 177-179.
44. Margaretha, P.; Tissot, P. Helv. Chim. Acta 1975, 58, 933-936.
45. Pirrung M. C.; Nunn, D. S. Tetrahedron Lett., 1992 33, 6591.
46. Others have also investigated this reaction with chiral diols: Corey, E. J.; Wu, L. I. J. Am. Chem. Soc. 1993, 115, 9327-9328.
47. de March, P.; Escoda, M.; Figueredo, M.; Font, J.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1995, 60, 3895-3897.
48. (a) Schuster, D. I.; Brisimitzakis, A. C. Tetrahedron Lett. 1982, 23, 4531-4534.
49. (b) Brisimitzakis, A. C.; Schuster, D. I. Tetrahedron Lett. 1982, 23, 4535-4538.
50. Depuy, C. H.; Lyons, C. E.; Rodewald, L. B. 1966, 11, 102-104.
51. Marx, J. N.; Cox, J. H.; Norman, L. R. J. Org. Chem. 1972, 37, 4489-4491.
52. Santry, L. J.; Azer, S.; McClelland, R. A. J. Am. Chem. Soc. 1988, 110, 2909-2914.
53. PCModel, Serena Software, P.O. Box 3076, Bloomington, IN 47402.
54. (a) Zimmerman, H. E.; Schuster, D. I. J. Am. Chem. Soc. 1961, 83, 4486-4488.
55. (b) Zimmerman, H. E.; Schuster, D. I. J. Am. Chem. Soc. 1962, 84, 4527-4540.
56. Fisch, M. H.; Richards, J. H. J. Am. Chem. Soc. 1963, 85, 3029-3030.
57. (a) Patel., D. J.; Schuster, D. I. J. Am. Chem. Soc. 1968, 90, 5137-5145.
58. (b) Zimmerman, H. E.; Lynch, D. C. J. Am. Chem. Soc. 1985, 107, 7745-7756.
59. (a) Schuster, D. I.; Fabian, A. C.; Kong, N. p.; Barringer, W. C.; Curran, W. V.; Sussman, H. D. J. Am. Chem. Soc. 1968, 90, 5027-5028.
60. (b) Schuster, D. I.; Brisimitzakis, A. C. J. Org. Chem. 1987, 52, 3644-3649.
61. (a) Chapman, O. L.; Weiss, D. S. Org. Photochem. 1973, 3, 205-209.
62. (a) Zimmerman, H. E.; Swenton, J. S. J. Am. Chem. Soc. 1964, 86, 1436-1437.
63. (b) Schuster, D. I.; Patel, D. J. J. Am. Chem. Soc. 1968, 90, 5145-5152.
64. Zimmerman, H. E.; Swenton, J. S. J. Am. Chem. Soc. 1967, 89, 906-912
65. Zimmerman, H. E.; Döpp, D.; Huyffer, P. S. J. Am. Chem. Soc. 1966, 88, 5352-5353.
66. Schuster, D, I.; Abraitys, V. Y. J. Chem. Soc., Chem. Commun. 1969, 419-420.
67. (a) Matoba, K.; Karibe, N.; Yamazaki, T. Chem. Pharm. Bull. 1982, 30, 3906-3911.
68. (b) Matoba, K.; Kawagoshi, F.; Tanabe, M.; Yamazaki, T. Chem. Pharm. Bull. 1985, 33, 3709-3714.
69. (c) Matoba, K.; Noda, H.; Yamazaki, T. Chem. Pharm. Bull. 1987, 35, 2627-2634.
70. (a) Samuel, C. J. J. Chem. Soc., Chem. Commun. 1979, 275-276.
71. (b) Samuel, C. J. J. Chem. Soc., Perkin Trans. 2 1981, 736-740.
72. Chapman, O. L.; Clardy, J. C.; McDowell, T. L.; Wright, H. E. J. Am. Chem. Soc. 1973, 95, 5086-5087.
73. Schuster, D. I.; Prabhu, K. U.; Smith, K. J.; van der Veen, J. M.; Fujiwara, H. Tetrahedron 1980, 36, 3495-3507.
74. Stille, J. K.; Rettig, T. A.; Kuemmerle, E. W., Jr. J. Org. Chem. 1976, 41, 2950-2955.
75. Zimmerman, H. E.; Pasteris, R. J. J. Org. Chem. 1980, 45, 4864-4876.
76. Schultz, A. G.; Harrington, R. E. J. Org. Chem. 1991, 56, 6391-6394.
77. Zimmerman, H. E.; Pasteris, R. J. J. Org. Chem. 1980, 45, 4876-4891.
78. Caine, D.; Powers, W. J., III; Alejandre, A. M. Tetrahedron Lett. 1968, 6071-6074.
79. Kropp, P. J. J. Am. Chem. Soc. 1964, 86, 4053-4061.
80. Kropp, P. J. Tetrahedron 1965, 21, 2183-2189.
81. (a) Caine, D.; Dawson, J. B. J. Org. Chem. 1964, 29, 3108-3110.
82. (b) Kropp, P. J. J. Org. Chem. 1964, 29, 3110-3111.
83. (a) Caine, D.; Tuller, F. N. J. Org. Chem. 1973, 38, 3663-3670.
84. (b) Caine, D.; Boucugnani, A. A.; Pennington, W. R. J. Org. Chem. 1976, 41, 3632-3634.
85. (c) Caine, D.; Boucugnani, A. A.; Chao, S. T.; Dawson, J. B.; Ingwalson, P. F. J. Org. Chem. 1976, 41, 1539-1544.
86. The lumiketone was also observed. Kropp, P. J.; Erman, W. F. J. Am. Chem. Soc. 1963, 85, 2456-2464.
87. Caine, D; DeBardeleben, J. F., Jr.; Dawson, J. B. Tetrahedron Lett. 1966, 3627-3634.
88. (a) Piers, E.; Cheng, K. F. J. Chem. Soc., Chem. Commun. 1969, 562-563.
89. (b) Piers, E.; Cheng, K. F. Can. J. Chem. 1970, 48, 2234-2235.
90. (c) Shiozaki, M.; Mori, K.; Matsui, M.; Hiraoka, T. Tetrahedron Lett. 1972, 657-660.
91. (d) Gasa, S.; Hamanaka, N.; Matsunaga, S.; Okuno, T.; Takeda, N.; Matsumoto, T. Tetrahedron Lett. 1976, 553-556.
92. Caine, D.; Brake, P. F.; DeBardeleben, J. F., Jr.; Dawson, J. B. J. Org. Chem. 1973, 38, 967-976.
93. Secor, H. V.; Bourlas, M.; DeBardeleben, J. F. Experientia, 1971, 27, 18-19.
94. The Electrosynthesis Co., Amherst, NY.
95. 4 should not be used as a drying agent. It causes significant hydrolysis to the monoketal.
96. Sakaino, M. Ph.D. Thesis, Cornell University, 1986.
97. See also: Sakaino, M.; Meinwald, J. Tetrahedron Lett. 1987, 28, 3201-3204.
98. Smith, L. I.; Austin, F. L. J. Am. Chem. Soc. 1942, 64, 528-533.
99. (a) Heller, J. E.; Dreiding, A. S.; O'Connor, B. R.; Simmons, H. E.; Buchanan, G. L.; Raphael, R. A.; Taylor, R. Helv. Chim. Acta 1973, 56, 272-280.
100. (b) Dolson, M. G.; Swenton, J. S. J. Org. Chem. 1981, 46, 177-179.
101. 2/HgO/PhH/hv has also been reported.
102. See: Goosen, A.; McCleland, C. W. J. Chem. Soc., Perkin Trans. 1 1978, 646-652.