Galloyl-derived orthoquinones as reactive partners in nucleophilic additions and Diels-Alder dimerizations: A novel route to the dehydrodigalloyl linker unit of agrimoniin-type ellagitannins

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6656-6665

  Feldman, Ken S ^a   Quideau, Stéphane ^a   Appel, Heidi M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELLAGITANNIN;

ARTICLE; BIOSYNTHESIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029842857     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961043u     Document Type: Article

References (97)

1. (a) Schmidt, O. T. Fortschr. Chem. Org. Naturstoffe 1956, 13, 70.
2. (b) Haslam, E. Plants polyphenols - Vegetable tannins revisited; Cambridge University Press: Cambridge, 1989.
3. (c) Okuda, T.; Yoshida, T.; Hatano. T. Phytochemistry 1993, 32, 507.
4. (d) Quideau, S.; Feldman, K. S. Chem. Rev. 1996, 96, 475.
5. (a) Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357.
6. (b) Feldman, K. S.; Ensel, S. M.; Minard, R. D. J. Am. Chem. Soc: 1994, 116, 1742.
7. (c) Feldman, K. S.; Sambandam, A. J. Org. Chem. 1995, 60, 8171.
8. (d) Feldman, K. S.; Smith, R. S. J. Org. Chem. 1996. 61, 2606.
9. (e) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2577.
10. (f) Lipshutz, B. H.: Liu, Z.-P.: Kayser, F. Tetrahedron Lett. 1994, 35. 5567.
11. (g) Itoh, T.; Chika, J.-i. J. Org. Chem. 1995, 60, 4968.
12. (a) Haslam, E. J. Nat. Prod. 1996, 59, 205-215.
13. (b) Haslam, E.; Lilley, T. H.; Cai, Y.; Martin, R.; Magnolato, D. Planta Med. 1989, 55, 1.
14. (c) Nishizawa, K.; Najata, I.; Kishida, A.; Ayer, W. A.; Browne, L. M. Phytochemistry 1990, 29, 2491.
15. (d) Kakiuchi, N.; Hattori, M.; Nishizawa, M.; Yamagishi, T.; Okuda, T.; Namba, T. Chem. Pharm. Bull. 1986, 34, 720.
16. (d) Ivancheva, S.; Manolova, N.; Serkedjieva, J.; Dimov, V.; Ivanovska, N. In Plant Polyphenols. Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; p 717.
17. (e) Serkedjieva, J.; Manolova, N. In Plant Polyphenols. Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; p 705.
18. (f) Okuda, T.; Yoshida, T.; Hatano, T. Planta Med. 1989, 55, 117.
19. (g) Okuda, T.; Yoshida, T.; Hatano, T. In Phenolic Compounds in Food and their Effects on Health, H; Huang, M.-T., Ho, C.-T., Lee, C. Y., Eds.; American Chemical Society: 1992; ACS Symposium Series 507; p 87.
20. (h) Okuda, T.; Yoshida, T.; Hatano, T. In Phenolic Compounds in Food and their Effects on Health, II; Huang, M.-T., Ho, C.-T., Lee, C. Y., Eds.; American Chemical Society: Washington, DC, 1992; ACS Symposium Series 507; p 160.
21. (i) Okuda, T.; Yoshida, T.; Hatano, T. In Plant Polyphenols. Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; p 539.
22. (j) Perchellet, J.-P.; Gali, H. U.; Perchellet, E. M.; Klish, D. S.; Armbrust, A. D. In Plant Polyphenols. Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; p 783.
23. (J) Yoshizawa, S.; Horiuchi, T.; Suganuma, M.; Nishiwaki, S.; Yatsunami, J.; Okabe, S.; Okuda, T.; Muto, Y.; Frenkel, K.; Troll, W.; Fujiki, H. In Phenolic Compounds in Food and their Effects on Health, II; Huang, M.-T., Ho, C.-T., Lee, C. Y., Eds.; American Chemical Society: Washington, DC, 1992; ACS Symposium Series 507; p 316.
24. (k) Miyamoto, K.; Kishi, N.; Koshiura, R.; Yoshida, T.; Hatano, T.; Okuda, T. Chem. Pharm. Bull. 1987, 35, 814.
25. (l) Berry, D. E.; MacKenzie, L.; Shultis, E. A.; Chan, J. A.; Hecht, S. M. J. Org Chem. 1992, 57, 420.
26. (m) Kashiwada, Y.; Nonaka, G.-I.; Nishioka, I.; Lee, K. J.-H.; Bori, I.; Fukushima, Y.; Bastow, K. F.; Lee, K.-H. J. Pharm. Sci 1993, 82, 487.
27. (n) Xie, L.; Xie, J.-X.; Kashiwada, Y.; Cosentino, L. M.; Liu, S.-H.; Pai, R. B.; Cheng, Y.-C.; Lee, K.-H. J. Med. Chem. 1995, 38, 3003.
28. (o) Kashiwada, Y.; Nonaka, G.-I.; Nishioka, I.; Chang, J.-J.; Lee, K.-H. J. Nat. Prod. 1992, 55, 1033.
29. (p) Tsai, Y. J.; Aoki, T.; Maruta, H.; Abe, H.; Sakagami, H.; Hatano, T.; Okuda, T.; Tanuma, S.-i. J. Biol. Chem. 1992, 267, 14436.
30. (q) Takechi, M.; Tanaka, Y.; Takehara, M.; Nonaka, G.-I.; Nishioka, I. Phytochemistry 1985, 24, 2245.
31. (r) Corthout, J.; Pieters, L. A.; Claeys, M.; Vanden Berghe, D. A.; Vlietinck, A. J. Phytochemistry 1991, 30, 1129.
32. (s) Fukuchi, K.; Sagakami, H.; Okuda, T.; Hatano, T.; Tanuma, S.; Kitajima, K.; Inoue, Y.; Inoue, S.; Ichikawa, S.; Nomomiya, M.; Konno, K. Antiviral Res. 1989, 11, 285.
33. (t) Nonaka, G.-I.; Nishioka, I.; Nishizawa, M.; Yamagishi, T.; Kashiwada, Y.; Dutschman, G. E.; Bodner, A. J.; Kilkuskie, R. E.; Cheng, Y.-C.; Lee, K.-H. J. Nat. Prod. 1990, 53, 587.
34. (u) Miyamoto, K.-i.; Nomura, M.; Murayama, T.; Furukawa, T.; Hatano, T.; Yoshida, T.; Koshiura, R.; Okuda, T. Biol. Pharm. Bull. 1993, 16, 379-387.
35. (v) Kakiuchi, N.; Hattori, M.; Namba. T.; Nishizawa, M.; Yamagishi, T.; Okuda, T. J. Nat. Prod. 1985, 48, 614.
36. (a) Okuda, T.; Yoshida, T.; Kuwahara, M.; Memon, M. U.; Shingu, T. J. Chem. Soc., Chem. Commun. 1982, 163.
37. (b) Okuda, T.; Yoshida, T.; Kuwahara, M.; Memon, M. U.; Shingu, T. Chem. Pharm. Bull. 1984, 32. 2165.
38. (c) Murayama, T.; Kishi, N.; Koshiura, R.; Tagaki, K.; Furukawa, T.; Miyamoto, K.-I. Anticancer Res. 1992, 12, 1471.
39. (d) Miyamoto, K.; Kishi, N.; Koshiura, R. Jpn. J. Pharmacol. 1987, 43, 187.
40. (e) Miyamoto, K.; Koshiura, R.; Ikeya, Y.; Taguchi, H. Chem. Pharm. Bull. 1985, 33, 3977-3981.
41. For an exception, see Jiang, Z.-H.; Tanaka, T.; Kouno, I. J. Chem. Soc., Chem. Commun. 1995, 1467.
42. Haslam, E.; Cai, Y. Nat. Prod. Rep. 1994, 41.
43. (a) Sugumaran, M.; Dali, H.; Semensi, V. Arch. Insect Biochem. Physiol. 1989, 11, 127.
44. (b) Sugumaran, M. Adv. Insect Physiol. 1988, 21, 179.
45. (c) Mason, H. S.; Peterson, E. W. Biochim. Biophys. Acta 1965, 111, 134, and references cited therein.
46. (d) Prota, G.; Scherillo, G.; Nicolaua, R. A. Gazz. Chim. Ital. 1968, 98, 495.
47. (e) Ito, S.; Prota, G. Experientia 1977, 33, 1118.
48. (f) Napolitano, A.; Costantini, C.; Crescenzi, O.; Prota, G. Tetrahedron Lett. 1994, 35, 6365.
49. (g) Thomson, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 305.
50. (h) Cheynier, V.; Trousdale, E. K.; Singleton, V. L.; Salgues, M. J.; Wylde, R. J. Agric. Food Chem. 1986, 34, 217.
51. (i) Salgues, M.; Cheynier, V.; Gunata, Z.; Wylde, R. J. Food Sci. 1986, 51, 1191.
52. (j) Walker, J. R. L.; Ferrar, P. H. Chem. Ind. 1995, 836, and references cited therein,
53. (k) Richard, F. C.; Goupy, P. M.; Nicolas, J. J.; Lacombe, J.-M.; Pavia, A. A. J. Agric. Food Chem. 1991, 39, 841, and references cited therein.
54. (l) Bambal, R. B.; Hanzlik, R. P. Chem. Res. Toxicol. 1995, 8, 729, and references cited therein.
55. (m) Pelizzetti, E.; Mentasti, E.; Pramauro, E. J. Chem. Soc., Perkin Trans. 2 1976, 1651.
56. (n) Tse, D. C. S.; McCreery, R. L.; Adams, R. N. J. Med. Chem. 1976, 19, 37, and references cited therein.
57. (o) Abul-Hajj, Y. J.; Tabakovic, K.; Gleason, W. B.; Ojala, W. H. Chem. Res. Toxicol. 1996, 9, 434.
58. (p) Iverson, S. L.; Shen, L.; Anlar, N.; Bolton, J. L. Chem. Res. Toxicol. 1996, 9, 492.
59. (q) Byck, J. S.; Dawson, C. R. Anal. Biochem. 1968, 25, 123.
60. (r) Liberate, D. J.; Byers, V. S.; Dennick, R. G.; Castagnoli, N. J. Med. Chem. 1981, 24, 28.
61. (a) Schultz, J. C.; Hunter, M. D.; Appel, H. M. In Plant Polyphenols. Synthesis, Properties. Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; p 621.
62. (b) Schultz, J. C.; Keating, S. T. In Microbial Mediation of Plant-Herbivore Interactions; Barbosa, P., Krischik, V. A., Jones, C. G., Eds.; Wiley: New York, 1991; Vol. 16, p 489.
63. (a) Tanaka, T.; Fujisaki, H.; Nonaka, G.; Nishioka, I. Heterocycles 1992, 33, 375.
64. (b) Tanaka, T.; Fujisaki, H.; Nonaka, G.-I.; Nishioka, I. Chem. Pharm. Bull. 1992, 40, 2937.
65. (a) Grundmann, C. In Methoden der Organischen Chemie (Houben-Weyl); Muller, E., Bayer, O., Eds.; Thieme: Stuttgart, 1979; Vol. VII/3b, part II, 1, and references cited therein.
66. (b) Kutyrev, A. A. Tetrahedron, 1991, 47, 8043, and references cited therein.
67. (c) Reinaud, O.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1985, 26, 3993.
68. Tabakovic, K.; Abul-Hajj, Y. J. Chem. Res. Toxicol. 1994, 7, 696.
69. Quideau, S.; Feldman, K. S.; Appel, H. M. J. Org. Chem. 1995, 60, 4982.
70. Horner, L.; Teichmann, K.-H.; Weber, K.-H.; Geyer, E. Chem. Ber. 1965, 98, 1233.
71. Wanzlick, H.-W. Chem. Ber. 1959, 92, 3006.
72. (a) Blomberg, C. Bull. Soc. Chim. Fr. 1972, 2143.
73. (b) Blomberg, C.; Grootveld, H. H.; Gerner, T. H.; Bickelhaupt, F. J. Organometal. Chem. 1970, 24, 549-553.
74. (c) Beak, P.; Yamamoto, J.; Upton, C. J. J. Org. Chem. 1975, 40, 3052.
75. Wege, D. Aust. J. Chem. 1971, 24, 1531.
76. a(2) = 10.0. Ackermann, G.; Hesse, D.; Volland, P. Z. Anorg. Allg. Chem. 1970, 377, 92.
77. (a) Yoshida, T.; Ahmed, A. H. F.; Memon, M. U.; Okuda, T. Phytochemistry 1993, 33, 197.
78. (b) Yoshida, T.; Maruyama, T.; Nitta, A.; Okuda, T. Chem. Pharm. Bull. 1992, 40, 1750.
79. 18b mp 141-146 °C (lit. 145-147 °C). (a) Kelly, T. R.; Montury, M. Tetrahedon Lett. 1978, 4311. (b) Lalancette, J. M.; Bessette, F.; Cliche, J. M. Can. J. Chem. 1966, 44, 1577.
80. 18b mp 141-146 °C (lit. 145-147 °C). (a) Kelly, T. R.; Montury, M. Tetrahedon Lett. 1978, 4311. (b) Lalancette, J. M.; Bessette, F.; Cliche, J. M. Can. J. Chem. 1966, 44, 1577.
81. Unpublished result, K. Sahasrabude, Pennsylvania state University.
82. (a) Stiles, B.; Burand, J. P.; Meda, M.; Wood, H. A. Appl. Environ. Microbiol. 1983, 297.
83. (b) Smith, I. R. L.; van Beek, N. A. M.; Podgwaite, J. D.; Wood, H. A. Gene 1988, 97.
84. (a) Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093.
85. (b) Bax, A.; Freeman, R. J. Magn. Reson. 1981, 44, 542.
86. (a) Bodenhausen, G.; Kogler, H.; Ernst, R. R. J. Magn. Reson. 1984, 58, 370.
87. (b) Davis, D. G. J. Magn. Reson. 1989, 81, 603.
88. (a) Scheline, R. R. Acta Chem. Scand. 1966, 20, 1182.
89. (b) Jurd, L. J. Am. Chem. Soc. 1959, 81, 4606.
90. Eisenhauer, H. R.; Link, K. P. J. Am. Chem. Soc. 1953, 75, 2046.
91. (a) Du Vigneau, V.; Miller, G. L. Biochem Prep. 1952, 2, 74.
92. (b) Ranganathan, S.; Jayaraman, N.; Roy, R. Tetrahedron 1992, 48, 931.
93. Neises, B.; Andries, T.; Steglich, W. J. Chem. Soc., Chem. Commun. 1982, 1132.
94. Zervas, L.; Photaki, I. J. Am. Chem. Soc. 1962, 84, 3887.
95. Shields, J. E.; Campbell, C. S.; Queener, S. W.; Duckworth, D. C.; Neuss, N. Helv. Chim. Acta 1984, 67, 870.
96. Jäger, G.; Geiger, R.; Siedel, W. Chem. Ber. 1968, 101, 3537.
97. Mayer, W. Liebigs Ann. Chem. 1952, 578, 34.