Total synthesis of (-)-corilagin

Journal of the American Chemical Society

Volumn 130, Issue 24, 2008, Pages 7566-7567

  Yamada, Hidetoshi ^a   Nagao, Kohei ^a   Dokei, Kazutoyo ^a   Kasai, Yusuke ^a   Michihata, Naoki ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CORILAGIN;

ARTICLE; DEMETHYLATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; RING OPENING;

GALLIC ACID; GLUCOSE; GLUCOSIDES; METHODS;

EID: 45249092488     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803111z     Document Type: Article

References (24)

1. (a) Gross, G. G.; Hemingway, R. W.; Yoshida, T., Eds. Plant Polyphenol 2. Chemistry, Biology, Pharmacology and Ecology; Kluwer Academic/Pleum Publishers: New York, 1999.
2. (b) Yoshida, T.; Hatano, T.; Ito, H.; Okuda, T. Studies in Natural Products Chemistry; Rahman, A.-u., Ed., Vol. 23, Elsevier Science: New York, 2000; pp 395-453..
3. Schmidt, O. T.; Lademann, R. Liebigs Ann. Chem. 1951, 571, 232-237.
4. Schmidt, O. T.; Schmidt, D. M.; Herok, J. Liebigs Ann. Chem. 1954, 587, 67-74.
5. Okuda, T.; Yoshida, T.; Hatano, T. Tetrahedron Lett. 1980, 21, 2561-2564.
6. (a) Shimizu, M.; Shiota, S.; Mizushima, T.; Ito, H.; Hatano, T.; Yoshida, T.; Tsuchiya, T. Antimicrob. Agents Chemother. 2001, 3198-3201.
7. (b) Liu, K. C.; Lin, M.; Lee, S.; Chiou, J.; Ren, S.; Lien, E. J. Planta Med. 1999, 65, 43-46.
8. (c) Okabe, S.; Suganuma, M.; Imayoshi, Y.; Taniguchi, S.; Yoshida, T.; Fujiki, H. Biol. Pharm. Bull. 2001, 24, 1145-1148.
9. (d) Adesina, S. K.; Idowu, O.; Ogundaini, A. O.; Oladimeji, H.; Olugbade, T. A.; Onawunmi, G. O.; Pais, M. Phytother. Res. 2000, 14, 371-374.
10. (e) Hwang, E.; Ahn, B.; Lee, H.; Kim, Y.; Lee, K.; Bok, S.; Kim, Y.; Kim, S. Planta Med. 2001, 67, 501-504.
11. (f) Cheng, J. R.; Lin, T. C.; Hsu, F. L. Can. J. Physiol. Pharmacol. 1995, 73, 1425-1429.
12. Ikeda, Y.; Nagao, K.; Tanigakiuchi, K.; Tokumaru, G.; Tsuchiya, H.; Yamada, H. Tetrahedron Lett. 2004, 45, 487-489.
13. (a) Quideau, S.; Feldman, K. S. Chem. Rev. 1996, 96, 475-503.
14. (b) Feldman, K. S. Phytochemistry 2005, 66, 1984-2000.
15. (c) Khanbabaee, K.; van Ree, T. Synthesis 2001, 1585-1610.
16. Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357-3366.
17. Feldman, K. S.; Sahasrabudhe, K. J. Org. Chem. 1999, 64, 209-216.
18. Pearson, A. J.; Bruhn, P. R. J. Org. Chem. 1991, 56, 7092-7097.
19. See Supporting Information.
20. Brussee, J.; Groenendijk, J. L. G.; te Koppele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313-3319.
21. (a) Zang, Y.; Yeung, S.-M.; Wu, H.; Heller, D. P.; Wu, C.; Wulff, W. D. Org. Lett. 2003, 5, 1813-1816.
22. (b) Smrčina, M.; Lorenc, M.; Hanus, V.; Sedmera, P.; Kočovský, P. J. Org. Chem. 1992, 57, 1917-1920.
23. (a) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4358.
24. (b) Tsubaki, K.; Miura, M.; Morikawa, H.; Tanaka, H.; Kawabata, T.; Furuta, T.; Tanaka, K.; Fuji, K. J. Am. Chem. Soc. 2003, 125, 16200-16201.