Redox active artificial ferrocenyl ellagitannins. Simple synthesis and their electrochemical properties

Chemistry Letters

Volumn , Issue 10, 1998, Pages 979-980

  Itoh, Toshiyuki ^a   Shirakami, Shohei ^a   Nakao, Yasuo ^a   Yoshida, Takashi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032279247     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.979     Document Type: Article

References (26)

1. For a review, see: T. Okuda, T. Yoshida, and T. Hatano, Photochemistry, 32, 507 (1993).
2. a) T. Ogata, and A. Kato, Kokai Tokkyo Koho, JP 04264026 A2 920918; Chem. Abstr., 118, 45735 (1992).
3. a) T. Ogata, and A. Kato, Kokai Tokkyo Koho, JP 04264026 A2 920918; Chem. Abstr., 118, 45735 (1992).
4. b) Y. Kashiwada, G. -I. Nonaka, I. Nishioka, J. -J. Chang, and K. -H. Lee, J. Nat. Prod., 55, 1033 (1992).
5. c) Y. Kashiwada, G. -I. Nonaka, I. Nishioka, J. -J. Chang, K. J. -H. Lee, I. Bori, Y. Fukushima, K. F. Bastow, and K. -H. Lee, J. Pharm. Sci., 82, 487 (1993).
6. d) K. Miyamoto, M. Nomura, T. Murayama, T. Furukawa, T. Hatano, T. Yoshida, R. Koshiura, and T. Okuda, Biol. Pharm. Bull., 16, 379 (1993).
7. For examples, see: a) K. S. Feldman, S. M. Ensel, and R. D. Minard, J. Am. Chem. Soc., 116, 1742 (1994).
8. b) T. Nelson and A. I. Meyers, J. Org. Chem., 59, 2577 (1994).
9. c) B. H. Lipshutz, Z. -P. Liu, and F. Kayser, Tetrahedron Lett., 35, 5567 (1994).
10. d) K. S. Feldmar, S. Quideau, and H. A. Appel, J. Org. Chem., 61, 6656 (1996).
11. e) K. Khanbabaee and K. Lötzerich, Liebigs Ann., 1571 (1997).
12. For recent reviews, see : a) S. A. Hudson and P. M. Maitlis, Chem. Rev. 93, 861 (1993).
13. b) M. Sawamura and Y. Ito, Chem. Rev., 92, 857 (1992).
14. c) A. Togni, Angew. Chem. Int. Ed. Engl., 35, 1475 (1996).
15. H. Tamura and M. Miwa, Chem. Lett., 1997, 1177.
16. a) T. Itoh and J. -I. Chika, J. Org. Chem., 60, 4968 (1995).
17. b) T. Itoh, J. -I. Chika, S. Shirakami, H. Ito, T. Yoshida, Y. Kubo, and J.-I. Uenishi, J. Org. Chem., 61, 3700 (1996).
18. Only (RD)-5 was obtained and no isomer was detected by HPLC analysis in the reaction.
19. Although (5D)-5 was obtained as major product, 18% (36%) of (RD)-5 was also formed (RD)-5 and (SD)-5 can be isolated using silica gel flash column chromatography.
20. 1H NMR analysis. Because anomeric epimerization at the C-1 position occurred during deprotection step of the benzylidene group under acidic conditions, and we failed to separate these isomers by silica gel flash column chromatography or silica gel TLC. Interestingly, no epimerization was observed when (RD)-5 was subjected to the same reaction.
21. Methyl gallate was polymerized under ambient atmospheric pressure in acetone in the presence of 1 eq. of dimethyl ester of ferrocene dicarboxylic acid 6, though more than 5 days was required to complete the reaction.
22. a) S. J. Sadeghi, G. Gilardi, G. Nicolosi, A. E. G. Cass, Chem. Commun., 1997, 517.
23. b) T. S. Marx-Tibbon, E. Katz, and I. Willner, J. Am. Chem. Soc., 117, 9925 (1995).
24. c) R. Blonder, E. Katz, I. Willner, V. Wray, and A. F. Bückmann, J. Am. Chem. Soc., 119, 11747 (1997), and references cited therein.
25. S. V. Javanovic, Y. Hara, S. Steenken, and M. G. Simic, J. Am. Chem. Soc., 117, 9881 (1995).
26. It is well known that the anion form of phenol compounds is easily oxidized and causes polymerization. For a review, see: R. Brouillard and R. Markakis, Ed. "Anthocyanins as Food Colors," Academic Press: New York (1982).