Synthesis of proanthocyanidins. Part 1. The first oxidative formation of the interflavanyl bond in procyanidins

Organic Letters

Volumn 10, Issue 17, 2008, Pages 3865-3868

  Achilonu, Matthew C ^a   Bonnet, Susan L ^a   Van Der Westhuizen, Jan H ^a  

^a UNIVERSITY OF THE FREE STATE   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

3'-O-METHYLCATECHIN; BIFLAVONOID; BORIC ACID; CATECHIN; CATECHIN 3' METHYL ETHER; DRUG DERIVATIVE; PHENOL DERIVATIVE; PROANTHOCYANIDIN; PROCYANIDIN B; SILVER DERIVATIVE; SILVER TETRAFLUOROBORATE;

ARTICLE; CHEMISTRY; DIMERIZATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

BIFLAVONOIDS; BORATES; CATECHIN; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; PHENOLS; PROANTHOCYANIDINS; SILVER COMPOUNDS; STEREOISOMERISM;

EID: 55949125363     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801353u     Document Type: Article

References (28)

1. Korkina, L. G.; Afanas'ev, I. B. ADV Pharmacol. 1997, 38, 151-163.
2. (a) Hertog, M. G.; Kromhout, D.; Aravanis, C.; Blackburn, H.; Buzina, R.; Fidanza, F.; Giampaoli, S.; Jansen, A.; Menotti, A.; Nedeljkovic, S. Arch. Intern. Med. 1995, 155, 381386;
3. (b) Knekt, P.; Jarvinen, R.; Reunanen, A.; Matela, J. BMJ 1996, 312, 478-481.
4. (a) Laughton, M. J.; Evans, P. J.; Morony, M.A.; Hoult, J. R.; Halliwell, B. Biochem. Pharmacol. 1991, 42, 1673-1681.
5. (b) Yoshimoto, T.; Furukawa, M.; Yamamoto, S.; Horie, T.; Watanabi-Kohno, S. Biochem. Biophys. Res. Commun. 1983, 116, 612-618.
6. Stefani, E. D.; Boffetta, P.; Deneo-Pellegrini, H. Nutr. Cancer 1999, 34, 100-110.
7. Hegarty, V. M.; May. H. M.; Khaw, K. T. Am. J. Clin. Nutr. 2000, 71, 1003-1007.
8. Wang, H. K.; Xia, Y.; Yang, Z. Y.; Natschke, S. L.; Lee, K. H. Adv. Exp. Med. Biol. 1998, 439, 191-225.
9. (a) Geissman, T. A.; Yoshiraura, N. N. Tetrahedron Lett. 1966, 7 (24), 2669-2773.
10. (b) Barrett, M. W.; Klyne, W.; Scopes, P. M.; Fletcher, A. C.; Porter, L. J.; Haslam, E. J. Chem. Soc., Perkin Trans. 1 1979, 2376.
11. (c) Botha, J. J.; Ferreira, D.; Roux, D. G. J. Chem. Soc., Chem. Commun. 1978, 698-513.
12. (d) Botha, J. J.; Young, D. A.; Ferreira, D.; Roux, D. G. J. Chem. Soc., Perkin Trans. 1 1981, 1213-1219.
13. (e) Botha, J. J.; Ferreira, D.; Roux, D. G. J. Chem. Soc., Perkin Trans. 1 1981, 1235-1244.
14. (f) Delcour, J. A.; Ferreira, D.; Roux, D. G. J. Chem. Soc., Perkin Trans. 1 1983, 1711-1717.
15. Botha, J. J.; Viviers, P. M.; Young, D. A.; Du Preez, I. C.; Ferreira, D.; Roux, D. G.; Hull, W. E. J. Chem. Soc., Perkin Trans. 1 1982, 527-533.
16. Young, D. A.; Kolodziej, H.; Ferreira, D.; Roux, D. G. J. Chem. Soc., Perkin Trans. 1 1985, 25372544.
17. (a) Steynberg, P. J.; Nel, R. J. J.; Van Rensburg, H.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron 1998, 8153-8158.
18. (b) Tückmantel, W.; Kozikowski, A. P.; Romanczyk, L. J. J. Am. Chem. Soc. 1999, 121, 12073-12081.
19. (c) Kozikowski, A. P.; Tückmantel, W.; George, C. J. Org. Chem. 2000, 65, 5371-5381.
20. (d) Saito, A.; Nakajima, N.; Tanaka, A.; Ubukata, M. Biosci. Biotechnol. Biochem. 2002, 66 (8), 1764-1767.
21. (e) Ohmori, K.; Nakajima, N.; Suzuki, K. PNAS 2004, 101 (33), 12002-12007.
22. (f) Mohri, Y.; Sagehashi, M.; Yamada, T.; Hattori, Y.; Morimura, K.; Kamo, T.; Hirota, M.; Makabe, H. Tetrahedron Lett. 2007, 48, 5891-5894.
23. Steenkamp, J. A.; Malan, J. C. S.; Ferreira, D. J. Chem. Soc., Perkin Trans. 1 1988, 2/7, 9-2183.
24. 2 and silica gel TLC yielded the desired products.
25. 16
26. 15,16
27. Van der Westhuizen, J. H.; Ferreira, D.; Roux, D. G. J. Chem. Soc., Ferkln Trans. 1 1981, 122, 0-1226,
28. Van der Westhuizen, J. H. 'n Nuwe Reeks Fotochemiese Reaksies in Flavonoïedsintese, Ph. D Thesis, 1979, 99.