Chemistry of epoxyquinols A, B, and C and epoxytwinol A

European Journal of Organic Chemistry

Volumn , Issue 23, 2007, Pages 3783-3800

  Shoji, Mitsuru ^a   Hayashi, Yujiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Density functional calculations; Diels Alder reactions; Electrocyclic reactions; Epoxyquinols A, B, C; Epoxytwinol A; Total synthesis

Indexed keywords

EID: 34547776294     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700092     Document Type: Short Survey

References (135)

1. a) J. Folkman, J. Natl. Cancer Inst. 1990, 82, 4;
2. b) W. Risau, Nature 1997, 386, 671;
3. c) M. Klagsbrum, M. A. Moses, Chem. Biol. 1999, 6, R217;
4. d) G. Gasparini, Drugs 1998, 58, 17.
5. H. Kakeya, R. Onose, H. Koshino, A. Yoshida, K. Kobayashi, S.-I. Kageyama, H. Osada, J. Am. Chem. Soc. 2002, 124, 3496.
6. H. Kakeya, R. Onose, A. Yoshida, H. Koshino, H. Osada, J. Antibiot. 2002, 55, 829.
7. H. Kakeya, H. Osada, unpublished results.
8. H. Kakeya, R. Onose, H. Koshino, H. Osada, Chem. Commun. 2005, 2575.
9. Y. Asami, H. Kakeya, R. Onose, A. Yoshida, H. Matsuzaki, H. Osada, Org. Lett. 2002, 4, 2845.
10. Y. Asami, H. Kakeya, R. Onose, Y.-H. Chang, M. Toi, H. Osada, Tetrahedron 2004, 60, 7085.
11. a) M. Shoji, J. Yamaguchi, H. Kakeya, H. Osada, Y. Hayashi, Angew. Chem. Int. Ed. 2002, 41, 3192;
12. b) M. Shoji, S. Kishida, M. Takeda, H. Kakeya, H. Osada, Y. Hayashi, Tetrahedron Lett. 2002, 43, 9155;
13. c) M. Shoji, H. Imai, M. Mukaida, K. Sakai, H. Kakeya, H. Osada, Y. Hayashi, J. Org. Chem. 2005, 70, 79.
14. Y. Hayashi, M. Shoji, J. Yamaguchi, K. Sato, S. Yamaguchi, T. Mukaiyama, K. Sakai, Y. Asami, H. Kakeya, H. Osada, J. Am. Chem. Soc. 2002, 124, 12078.
15. J. Yamaguchi, M. Toyoshima, M. Shoji, Y. Hayashi, H. Kakeya, H. Osada, Angew. Chem. Int. Ed. 2006, 45, 789.
16. For a review of naturally occurring cyclohexane epoxides, see: J. Marco-Contelles, M. T. Molina, S. Anjum, Chem. Rev. 2004, 104, 2857.
17. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons, Chichester, 1976.
18. For a review of biomimetic electrocyclizations, see: C. M. Beaudry, J. P. Malerich, D. Trauner, Chem. Rev. 2005, 105, 4757;
19. for biosynthetic Diels-Alder reactions, see: E. M. Stocking, R. M. Williams, Angew. Chem. Int. Ed. 2003, 42, 3078.
20. a) C. Li, S. Bardhan, E. A. Pace, M.-C. Liang, T. D. Gilmore, J. A. Porco Jr, Org. Lett. 2002, 4, 3267;
21. b) C. Li, J. A. Porco Jr, J. Org. Chem. 2005, 70, 6053.
22. a) G. Mehta, K. Islam, Tetrahedron Lett. 2003, 44, 3569;
23. b) G. Mehta, K. Islam, Tetrahedron Lett. 2004, 45, 3611.
24. S. Kuwahara, S. Imada, Tetrahedron Lett. 2005, 46, 547.
25. C. Li, J. A. Porco Jr, J. Am. Chem. Soc. 2004, 126, 1310.
26. a) J. C. Lee, X. Yang, M. Schwartz, G. Strobel, J. Clardy, Chem. Biol. 1995, 2, 721;
27. b) J. C. Lee, G. A. Strobel, E. Lobkovsky, J. Clardy, J. Org. Chem. 1996, 61, 3232;
28. c) B. B. Jarvis, Chem tracts: Org. Chem. 1997, 10, 10.
29. a) C. Li, E. Lobkovsky, J. A. Porco Jr, J. Am. Chem. Soc. 2000, 122, 10484;
30. b) C. Li, R. P. Johnson, J. A. Porco Jr, J. Am. Chem. Soc. 2003, 125, 5095.
31. G. Mehta, S. C. Pan, Org. Lett. 2004, 6, 3985.
32. G. Sarakinos, E. J. Corey, Org. Lett. 1999, 1, 1741.
33. a) M. Shoji, S. Kishida, Y. Kodera, I. Shiina, H. Kakeya, H. Osada, Y. Hayashi, Tetrahedron Lett. 2003, 44, 7205;
34. b) M. Shoji, H. Imai, I. Shiina, H. Kakeya, H. Osada, Y. Hayashi, J. Org. Chem. 2004, 69, 1548.
35. E. N. Marvell, Thermal Electrocyclic Reactions, Academic Press, New York, 1980.
36. For a recent review of asymmetric Diels-Alder reactions, see: Y. Hayashi, "Catalytic Asymmetric Diels-Alder Reactions" in Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi, K. A. Jørgensen), Wiley-VCH, Weinheim, 2001, pp. 5-56;
37. for a review of Diels-Alder reactions of furan, see: C. O. Kappe, S. S. Murphree, A. Padwa, Tetrahedron 1997, 53, 14179;
38. for a review of optically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives, see P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 173.
39. Catalytic asymmetric reaction by the use of a chiral Lewis acid: a) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979;
40. b) I. Yamamoto, K. Narasaka, Chem. Lett. 1995, 1129;
41. c) D. A. Evans, D. M. Barnes, Tetrahedron Lett. 1997, 38, 57;
42. diastereoselective reaction by the use of chiral dienophiles: d) H. Takayama, A. Iyobe, T. Koizumi, J. Chem. Soc. Chem. Commun. 1986, 771;
43. e) J. M. Fraile, J. I. García, D. Gracia, J. A. Mayoral, E. Pires, J. Org. Chem. 1996, 61, 9479;
44. f) J. Adrio, J. C. Carretero, J. L. G. Ruano, L. M. M. Cabrejas, Tetrahedron: Asymmetry 1997, 8, 1623;
45. g) O. Arjona, F. Iradier, R. Medel, J. Plumet, Tetrahedron: Asymmetry 1999, 10, 2237;
46. h) M. J. Burke, M. M. Allan, M. Parvez, B. A. Keay, Tetrahedron: Asymmetry 2000, 11, 2733, and references cited therein.
47. Y. Hayashi, M. Nakamura, S. Nakao, T. Inoue, M. Shoji, Angew. Chem. Int. Ed. 2002, 41, 4079.
48. D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1988, 110, 1238.
49. a) M. M. Campbell, A. D. Kaye, M. Sainsbury, R. Yavarzadeh, Tetrahedron Lett. 1984, 25, 1629;
50. b) M. M. Campbell, A. D. Kaye, M. Sainsbury, R. Yavarzadeh, Tetrahedron 1984, 40, 2461.
51. D. Rajapaksa, B. A. Keay, R. Rodrigo, Can. J. Chem. 1984, 62, 826.
52. 3): S. Ogawa, M. Yoshikawa, T. Taki, J. Chem. Soc. Chem. Commun. 1992, 406.
53. a) T. Sugai, Curr. Org. Chem. 1999, 3, 373;
54. b) K.-i. Fuhshuku, S. Oda, T. Sugai, Recent Res. Devel. Org. Chem. 2002, 6, 57.
55. For the Diels-Alder reaction of methyl acrylate and furan, see: a) H. Kotsuki, K. Asao, H. Ohnishi, Bull. Chem. Soc. Jpn. 1984, 57, 3339;
56. b) J. A. Moore, E. M. Partain III, J. Org. Chem. 1983, 48, 1105;
57. c) F. Brion, Tetrahedron Lett. 1982, 23, 5299;
58. d) J. M. Fraile, J. I. García, J. Massam, J. A. Mayoral, E. Pires, J. Mol. Catal. A 1997, 123, 43;
59. e) D. J. Ager, M. B. East, Heterocycles 1994, 37, 1789;
60. for the Diels-Alder reaction under high pressure, see: f) H. Kotsuki, H. Nishizawa, M. Ochi, K. Matsuoka, Bull. Chem. Soc. Jpn. 1982, 55, 496;
61. g) W. G. Dauben, H. O. Krabbenhoft, J. Am. Chem. Soc. 1976, 98, 1992;
62. for the Diels-Alder reaction of acrylic acid and furan, see: h) T. Suami, S. Ogawa, K. Nakamoto, I. Kasahara, Carbohydr. Res. 1977, 58, 240, and references therein.
63. Jennings-White and Holmes et al. have elegantly synthesized cis-maneonene A using a similar sequence involving the Diels-Alder reaction of furan and fumaryl chloride followed by hydrolysis and bromolactonization; see: C. L. D. Jennings-White, A. B. Holmes, P. R. Raithby, J. Chem. Soc. Chem. Commun. 1979, 542.
64. I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092.
65. a) K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95, 6136;
66. b) R.-M. Meier, C. Tamm, Helv. Chim. Acta 1991, 74, 807.
67. J. R. Parikh, W. v. E. Doering, J. Am. Chem. Soc. 1967, 89, 5505.
68. In our previous paper, Dess-Martin periodinane was employed as the oxidant which gave the desired product in good yield. TEMPO oxidation is suitable for large-scale preparation. P. L. Anelli, F. Montanari, S. Quici, Org. Synth. 1993, Coll. Vol. 8, 367.
69. P. Yadagiri, S. Lumin, P. Mosset, J. Capdevila, J. R. Falck, Tetrahedron Lett. 1986, 27, 6039.
70. M. T. Barros, C. D. Maycock, M. R. Ventura, Chem. Eur. J. 2000, 6, 3991.
71. C.-K. Sha, S.-J. Huang, Tetrahedron Lett. 1995, 36, 6927.
72. J. M. McIntosh, Can. J. Chem. 1971, 49, 3045.
73. R. Benhida, P. Blanchard, J.-L. Fourrey, Tetrahedron Lett. 1998, 39, 6849.
74. a) A. S.-Y. Lee, W.-C. Dai, Tetrahedron 1997, 53, 859;
75. b) D. S. Matteson, P. K. Jesthi, J. Organomet. Chem. 1976, 110, 25.
76. F. S. Ruel, M. P. Braun, C. R. Johnson, Org. Synth. 1997, 75, 69.
77. Y. Hu, C. Li, B. A. Kulkarni, G. Strobel, E. Lobkovsky, R. M. Torczynski, J. A. Porco Jr, Org. Lett. 2001, 3, 1649.
78. All calculations were performed with the program package: TITAN 1.0.5, Schrödinger Inc. (http://www.schrodinger.com) and Wavefunction Inc. (http://www.wavefun.com).
79. J. Rodríguez-Otero, J. Org. Chem. 1999, 64, 6842.
80. R. B. Woodward, R. Hoffmann, The conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970.
81. a) C.-H. Chou, W. S. Trahanovsky, J. Am. Chem. Soc. 1986, 108, 4138;
82. b) G. Simig, M. Schlosser, Tetrahedron Lett. 1994, 35, 3081;
83. c) M.-k. Leung, W. S. Trahanovsky, J. Am. Chem. Soc. 1995, 117, 841.
84. J. B. Foresman, Æ. Frisch in Exploring Chemistry with Electron Structure Methods, Gaussian, Inc., Pittsburgh, PA, 1996.
85. a) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785;
86. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
87. a) Diels-Alder reaction: E. Goldstein, B. Beno, K. N. Houk, J. Am. Chem. Soc. 1996, 118, 6036;
88. b) Diels-Alder reaction: O. Wiest, D. C. Montiel, K. N. Houk, J. Phys. Chem. A 1997, 101, 8378;
89. c) Diels-Alder reaction, Cope rearrangement, [5,5] sigmatropic rearrangement: K. N. Houk, B. R. Beno, M. Nendel, K. Black, H. Y. Yoo, S. Wilsey, J. K. Lee, THEOCHEM 1997, 398-399, 169;
90. d) [5,5] sigmatropic rearrangement: B. R. Beno, J. Fennen, K. N. Houk, H. J. Lindner, K. Hafner, J. Am. Chem. Soc. 1998, 120, 10490;
91. e) retro-Diels-Alder reaction and [1,3] sigmatropic rearrangement: B. R. Beno, S. Wilsey, K. N. Houk, J. Am. Chem. Soc. 1999, 121, 4816;
92. f) Bergman cyclization: J. Gräfenstein, A. M. Hjerpe, E. Kraka, D. Cremer, J. Phys. Chem. A 2000, 104, 1748;
93. g) 1,3-dipolar cycloaddition of nitrone: C. D. Valentin, M. Freccero, R. Gandolfi, A. Rastelli, J. Org. Chem. 2000, 65, 6112;
94. h) Bergman cyclization: E. Kraka, D. Cremer, J. Comput. Chem. 2001, 22, 216;
95. i) Diels-Alder reaction: G. Orlova, J. D. Goddard, J. Org. Chem. 2001, 66, 4026;
96. j) transformation of 2-carbenabicyclo[3.2.1]octa-3,6-diene: P. K. Freeman, J. K. Pugh, J. Org. Chem. 2001, 66, 5338;
97. k) 1,3-dipolar addition: K. Kavitha, P. Venuvanalingam, J. Chem. Soc. Perkin Trans. 2 2002, 2130;
98. l) [6+4] cycloaddition: A. G. Leach, E. Goldstein, K. N. Houk, J. Am. Chem. Soc. 2003, 125, 8330;
99. m) cycloaddition of thiobenzophenone S-methylide: R. Sustmann, W. Sicking, R. Huisgen, J. Am. Chem. Soc. 2003, 125, 14425;
100. n) dimerization of nitrile oxide: Z.-X. Yu, P. Caramella, K. N. Houk, J. Am. Chem. Soc. 2003, 125, 15420;
101. o) Cope rearrangement: J. J. Blavins, D. L. Cooper, P. B. Karadakov, J. Phys. Chem. A 2004, 108, 194;
102. p) isomerizations of bicyclopentene and tricyclopentane to cyclopentadiene: I. Özkan, A. Kinal, M. Balci, J. Phys. Chem. A 2004, 108, 507;
103. q) [2+2] cycloaddition: S. M. Bachrach, J. C. Gilbert, J. Org. Chem. 2004, 69, 6357;
104. r) cycloaddition of thiobenzophenone S-methylide: R. Sustmann, W. Sicking, R. Huisgen, Eur. J. Org. Chem. 2005, 1505;
105. s) Bergman cyclization: J. C. Santos, J. Andres, A. Aizman, P. Fuentealba, V. Polo, J. Phys. Chem. A 2005, 109, 3687.
106. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.05, Gaussian, Inc., Pittsburgh, PA, 2003.
107. I. Shiina, T. Uchimaru, M. Shoji, H. Kakeya, H. Osada, Y. Hayashi, Org. Lett. 2006, 8, 1041.
108. S. F. Boys, F. Bernardi, Mol. Phys. 1970, 19, 553.
109. R. Sekizawa, S. Ikeno, H. Nakamura, H. Naganawa, S. Matsui, H. Iinuma, T. Takeuchi, J. Nat. Prod. 2002, 65, 1491.
110. a) D. C. Swinney, Drug Discovery Today 2001, 6, 244;
111. b) C. M. Pickart, Annu. Rev. Biochem. 2001, 70, 503;
112. c) M. H. Glickman, A. Ciechanover, Physiol. Rev. 2002, 82, 373;
113. d) A. Ciechanover, Cell Death Differ. 2005, 12, 1178.
114. X. Lei, R. P. Johnson, J. A. Porco Jr, Angew. Chem. Int. Ed. 2003, 42, 3913.
115. a) J. E. Moses, L. Comméiras, J. E. Baldwin, R. M. Adlington, Org. Lett. 2003, 5, 2987;
116. b) L. Comméiras, J. E. Moses, R. M. Adlington, J. E. Baldwin, A. R. Cowley, C. M. Baker, B. Albrecht, G. H. Grant, Tetrahedron 2006, 62, 9892.
117. a) G. Mehta, S. S. Ramesh, Tetrahedron Lett. 2004, 45, 1985;
118. b) G. Mehta, K. Islam, Tetrahedron Lett. 2004, 45, 7683.
119. a) Y. Hayashi, J. Yamaguchi, T. Sumiya, M. Shoji, Angew. Chem. Int. Ed. 2004, 43, 1112;
120. b) Y. Hayashi, J. Yamaguchi, T. Sumiya, K. Hibino, M. Shoji, J. Org. Chem. 2004, 69, 5966;
121. c) Y. Hayashi, J. Yamaguchi, K. Hibino, T. Sumiya, T. Urushima, M. Shoji, D. Hashizume, H. Koshino, Adv. Synth. Catal. 2004, 346, 1435;
122. for papers by other groups, see: d) G. Zhong, Angew. Chem. Int. Ed. 2003, 42, 4247;
123. e) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808;
124. f) A. Bøgevig, H. Sundén, A. Córdova, Angew. Chem. Int. Ed. 2004, 43, 1109;
125. g) A. Córdova, H. Sundén, A. Bøgevig, M. Johansson, F. Himo, Chem. Eur. J. 2004, 10, 3673;
126. h) N. Momiyama, H. Torii, S. Saito, H. Yamamoto, Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5374;
127. i) W. Wang, J. Wang, H. Li, L. Liao, Tetrahedron Lett. 2004, 45, 7235;
128. j) for a review, see: P. Merino, T. Tejero, Angew. Chem. Int. Ed. 2004, 43, 2995;
129. k) H. Yamamoto, N. Momiyama, Chem. Commun. 2005, 3514.
130. M. Matsuzawa, H. Kakeya, J. Yamaguchi, M. Shoji, R. Onose, H. Osada, Y. Hayashi, Chem. Asian J. 2006, 1, 845.
131. B. Schlegel, A. Härtl, H.-M. Dahse, F. A. Gollmick, U. Gräfe, H. Dörfelt, B. Kappes, J. Antibiot. 2002, 55, 814.
132. J. J. La Clair, Angew. Chem. Int. Ed. 2006, 45, 2769.
133. S. D. Rychnovsky, Org. Lett. 2006, 8, 2895.
134. J. A. Porco Jr, S. Su, X. Lei, S. Bardhan, S. D. Rychnovsky, Angew. Chem. Int. Ed. 2006, 45, 5790.
135. Preliminary results have been published: H. Kakeya, Y. Miyake, M. Shoji, S. Kishida, Y. Hayashi, T. Kataoka, H. Osada, Bioorg. Med. Chem. Lett. 2003, 13, 3743.