Ellagitannin Chemistry. the First Synthesis of Dehydrohexahydroxydiphenoate Esters from Oxidative Coupling of Unetherified Methyl Gallate

Journal of Organic Chemistry

Volumn 62, Issue 25, 1997, Pages 8809-8813

  Quideau, Stéphane ^a,b   Feldman, Ken S ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001367025     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971354k     Document Type: Article

References (60)

1. (a) Quideau, S.; Feldman, K. S. Chem. Rev. (Washington, D.C.) 1996, 96, 475 and references therein.
2. (b) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2577.
3. Lipshutz, B. H.; Liu, Z.-P.; Kayser, F. Tetrahedron Lett. 1994, 35, 5567.
4. Okuda, T.; Yoshida, T.; Hatano, T. Prog. Chem. Org. Nat. Prod. 1995, 66, 1.
5. Feldman, K. S.; Quideau, S.; Appel, H. M. J. Org. Chem. 1996, 61, 6656.
6. (a) Feldman, K. S.; Ensel, S. M.; Minard, R. D. J. Am. Chem. Soc. 1994, 116, 1742.
7. (b) Feldman, K. S.; Sambandam, A. J. Org. Chem. 1995, 60, 8171.
8. Feldman, K. S.; Smith, R. S. J. Org. Chem. 1996, 61, 2606.
9. (a) Okuda, T.; Yoshida, T.; Hatano, T. J. Chem. Soc., Perkin Trans. 1 1982, 9.
10. (b) Okuda, T.; Yoshida, T.; Hatano, T. Tetrahedron Lett. 1980, 21, 2561.
11. Okuda, T.; Nayeshiro, H.; Seno, K. Tetrahedron Lett. 1977, 4421.
12. Okuda, T.; Yoshida, T.; Nayeshiro, H. Chem. Pharm. Bull. 1977, 25, 1862.
13. (e) Okuda, T.; Yoshida, T.; Nayeshiro, H. Tetrahedron Lett. 1976, 3721.
14. (f) Haddock, E. A.; Gupta, R. K.; Haslam, E. J. Chem. Soc., Perkin Trans. 1 1982, 2535.
15. Schmidt, O. T.; Wieder, G. Liebigs Ann. Chem. 1967, 706, 198.
16. (a) Okuda, T.; Hatano, T.; Nitta, H.; Fujii, R. Tetrahedron Lett. 1980, 21, 4361.
17. (b) Yazaki, K.; Hatano, T.; Okuda, T. J. Chem. Soc., Perkin Trans. 1 1989, 2289.
18. (a) Yoshida, T.; Arioka, H.; Fujita, T.; Chen, X.-M.; Okuda, T. Phytochemistry 1994, 37, 863.
19. (b) Okuda, T.; Hatano, T.; Yasui, T. Heterocycles 1981, 16, 1321.
20. Nonaka, G.-i.; Matsumoto, Y.; Nishioka, I. Chem. Pharm. Bull. 1981, 29, 1184.
21. Quideau, S.; Feldman, K. S.; Appel, H. M. J. Org. Chem. 1995, 60, 4982.
22. (a) Löwe, J. F. F. F. Z. Chem. 1868, 4, 603.
23. (b) Ernst, F.; Zwenger, C. Annalen 1871, 159, 32.
24. Perkin A. G.; Nierestein, M. J. Chem. Soc. 1905, 87, 1412.
25. Perkin, A. G. J. Chem. Soc. 1906, 89, 251.
26. (e) Erdtman, H. Svensk Kern. Tidskr. 1935, 47, 223.
27. (f) Mayer, W. Annalen 1952, 578, 34.
28. (g) Hathway, D. E. J. Chem. Soc. 1957, 519.
29. (h) Jurd, L. J. Am. Chem. Soc. 1959, 81, 4606.
30. Pastuska, G. Naturwissenschaften 1961, 48, 457
31. (j) Mayer, W.; Hoffmann, E. H.; Lösch, N.; Wolf, H.; Wolter, B.; Schilling G. Annalen 1984, 929.
32. (k) Zeng, W.; Heur, Y.-H.; Kinstle, T. H.; Stoner, G. D. Labeled Cmpd. 1991, 29, 657.
33. Hathway, D. E. Biochem. J. 1957, 67, 445.
34. Flaig, W.; Haider, K. Planta Med. 1961, 9, 123.
35. (n) Kamel, M. Y.; Saleh, N. A.; Ghazy, A. M. Phytochemistry 1977, 16, 521
36. (o) Pospisil, F.; Cvikrová, M.; Hrubcová, M. Biochem. Plantar. (Praha) 1983, 25, 373.
37. (p) Gross, G. In Plant Polyphenols. Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; pp 43-60.
38. (q) Gupta, R. K.; Al-Shafi, S. M. K.; Layden, K.; Haslam, E. J. Chem. Soc., Perkin Trans. 1 1982, 2525.
39. (a) Schmidt, O. T.; Schanz, R.; Eckert, R.; Wurmb, R. Liebigs Ann. Chem. 1967, 706, 131.
40. (b) Schmidt, O. T.; Schanz, R.; R., W.; Groebke, W. Liebigs Ann. Chem. 1967, 706, 154.
41. Schmidt, O. T.; Schulz, J.; Wurmb, R. Liebigs Ann. Chem. 1967, 706, 169.
42. (a) Musso, H. Angew. Chem., Int. Ed. Engl. 1963, 2, 723.
43. (b) Critchlow, A.; Halslam, E.; Haworth, R. D.; Tinker, P. B.; Waldron, N. M. Tetrahedron 1967, 23, 2829.
44. Perkin, A. G.; Steven, A. B. J. Chem. Soc. 1906, 802.
45. Teuber, H.-J.; Steinmetz, G. Chem. Ber. 1965, 98, 666.
46. (e) Teuber, H.-J.; Heinrich, P.; Dietrich, M. Liebigs Ann. Chem. 1966, 696, 64. The pyrogallol-derived orthoquinone i dimerizes as shown to furnish the "head-to-tail" dimer ii, a distinct regioisomer of the "head-to-head" structure of galloyl orthoquinone dimer 6. The assignment of connectivity shown in 6 is preferred over an alternative iii since no three-bond HMBC response between the hydroxyl protons OH-5/5′ at 5.86 ppm and the protonated carbons C-1/1′ was observed, as would be expected for iii.
47. (a) Schmidt, O. T.; Voigt, H.; Puff, W.; Köster, R. Liebigs Ann. Chem. 1954, 586, 165.
48. (b) Schmidt, O. T., Demmler, M. Liebigs Ann. Chem. 1954, 586, 179.
49. Itoh, T.; Chika, J.-i.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J.-i. J. Org. Chem. 1996, 61, 3700.
50. Bax, A.; Freeman, R. J. Magn. Reson. 1981, 44, 542.
51. (a) Tanaka, T.; Fujisaki, H.; Nonaka, G.-I.; Nishioka, I. Chem. Pharm. Bull. 1992, 40, 2937.
52. (b) Tanaka, T.; Fujisaki, H.; Nonaka, G.-i.; Nishioka, I. Heterocycles 1992, 33, 375.
53. Tanaka, T.; Kouno, I.; Nonaka, G.-i. Chem. Pharm. Bull. 1996, 44, 34.
54. (a) Haslam, E.; Cai, Y. Nat. Prod. Rep. 1994, 41.
55. (b) Waters, W. A. J. Chem. Soc. B 1971, 2026.
56. Doddrell, D. M.; Pegg, D. T.; Bendall, M. R. J. Magn. Reson. 1982, 48, 323.
57. Bax, A.; Subramanian, S. J. Magn. Reson. 1986, 67, 565.
58. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093.
59. (a) Schmidt, O. T.; Demmler, K. Liebigs Ann. Chem. 1952, 576, 85.
60. (b) Herzig, J.; Polak, J. Monatsch. Chem. 1908, 29, 263.