Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea

Organic Letters

Volumn 3, Issue 5, 2001, Pages 739-741

  Li, Lianhai ^a   Chan, Tak Hang ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CATECHIN; DRUG DERIVATIVE; EPIGALLOCATECHIN GALLATE;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS; TEA;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CATECHIN; OXIDATION-REDUCTION; STEREOISOMERISM; TEA;

EID: 0035826349     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000394z     Document Type: Article

References (21)

1. For selected recent reviews, see: (a) Bushman, J. L. Nutr. Cancer 1998, 31, 151.
2. (b) Weisburger, J. H. Proc. Soc. Exp. Biol. Med. 1999, 220, 271.
3. (c) Hollman, P. C.; Feskens, E. J.; Katan, M. B. Proc. Soc. Exp. Biol. Med. 1999, 220, 198.
4. (d) Stensvold, I.; Tverdal, A.; Solvoll, K.; Per Foss O. Prev. Med. 1992, 21, 546.
5. Haslam, E. Plant Polyphenols. Vegetable Tannins Revisited. Cambridge University Press: Cambridge, 1989.
6. The effect of the nonpolyphenolic fraction of green tea leaves has recently been studied: Higashi-Okai, K.; Otani, S.; Okai, Y. Cancer Lett. 1998, 129, 223.
7. Otsuka, T.; Ogo, T.; Eto, T.; Asano, Y.; Suganuma, M.; Niho, Y. Life Sci. 1998, 63, 1397.
8. Valcic, S.; Timmermann, B. N.; Alberts, D. S.; Watcher, G. A.; Krutzsch, M.; Wymer, J.; Guillen, J. M. Anticancer Drugs 1996, 7, 461.
9. Paschka, A. G.; Butler, R.; Young, C. Y. Cancer Lett. 1998, 130, 1.
10. Asano, T.; Okamura, S.; Ogo, T.; Eto, T.; Otsukat, T.; Niho, Y. Life Sci. 1997, 60, 135.
11. Liang, Y. C.; Lin-Shiau, S. Y.; Chen, C. F.; Lin, J. K. J. Cell. Biochem. 1997, 67, 55.
12. Kelloff, G. J.; Crowell, J. A.; Hawk, E. T.; Steele, V. E.; Lubet, R. A.; Boone, C. W.; Covey, J. M.; Doody, L. A.; Omenn, G. S.; Greenwald, P.; Hong, W. K.; Parkinson, D. R.; Bagheri, D.; Baxter, G. T.; Blunden, M.; Doeltx, M. K.; Eisenhauer, K. M.; Johnson, K.; Knapp, G. G.; Longfellow, D. G.; Malone, W. F.; Nayfield, S. G.; Seifried, H. E.; Swall, L. M.; Sieman, C. C. J. Cell. Biochem. Suppl. 1996, 26, 54.
13. For the syntheses of simpler catechins, see: (a) Keogh, E. J.; Philbin, E. M. Chem. Ind. 1961, 2100.
14. (b) Jain, A. C.; Prabhat, A.; Nayyar, N. K. Indian J. Chem. 1983, 22B, 1116.
15. (c) van Rensburg, H.; van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron Lett. 1997, 38, 3089.
16. (d) van Rensburg, H.; van Heerden, P. S.; Ferreira, D. J. Chem. Soc., Perkin Trans. 1 1997, 3415.
17. (e) Jew, S.; Kim, H.; Bae, S.; Kim, J.; Park, H. Tetrahedron Lett. 2000, 41, 7925.
18. (f) Nay, B.; Monti, J.-P.; Nuhrich, A.; Deffieux, G.; Merillon, J.-M.; Vercauteren, J. Tetrahedron Lett. 2000, 41, 9049.
19. The sequence Dess-Martin oxidation/L-Selectride reduction has previously been applied to the stereochemical inversion at C-3 of 5,7,3′,4′-tetra-O-benzylcatechin: Tuckmantel, W.; Kozikowski, A. P.; Romanczyk, L. J., Jr. J. Am. Chem. Soc. 1999, 121, 12073.
20. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
21. 1H NMR spectra as the (-)-isomer.