An improved synthesis of procyanidin dimers: Regio- and stereocontrol of the interflavan bond

European Journal of Organic Chemistry

Volumn , Issue 23, 2006, Pages 5367-5377

  Tarascou, Isabelle ^a   Barathieu, Karine ^a,b   André, Yann ^a,b   Pianet, Isabelle ^a   Dufourc, Erick J ^b   Fouquet, Eric ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b INSTITUT EUROPÉEN DE CHIMIE ET BIOLOGIE   (France)

Author keywords

Oligomerization; Polyphenol; Procyanidin dimer; Stereoselectivity; Synthetic methods

Indexed keywords

EID: 33845461934     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600668     Document Type: Article

References (49)

1. C. Simon, K. Barathieu, M. Laguerre, J. M. Schmitter, E. Fouquet, I. Pianet, E. J. Dufourc, Biochemistry 2003, 42, 10385-10395.
2. E. Haslam, J. Nat. Prod. 1996, 59, 205-215.
3. C. Prieur, J. Rigaud, V. Cheynier, M. Moutounet, Phytochemistry 1994, 36, 781-784.
4. a) P. Ribéreau-Gayon, Ann. Physiol. Vég. 1964, 6, 211-242;
5. b) J. M. Souquet, V. Cheynier, F. Brossaud, M. Moutounet, Phytochemistry 1996, 43, 509-512.
6. P. Ribéreau-Gayon, Y. Glories, A. Maujean, D. Dubourdieu, Traité d'œnologie, vol. 2, Chimie du vin, stabilisation et traitements, Dunod, Paris, 1998.
7. a) S. Renaud, M. de Lorgeril, Lancet 1992, 339, 1523-1526;
8. b) G. J. Soleas, E. P. Diamandis, D. M. Goldberg, J. Clin. Lab. An. 1997, 11, 287-313;
9. c) M. Nakao, S. Takio, K. Ono, Phytochemistry 1998, 49, 2379-2382.
10. a) K. Weinges, J. Perner, Chem. Commun. (London) 1967, 351-352;
11. b) A. P. Kozikowski, W. Tückmantel, Y. Hu, J. Org. Chem. 2001, 66, 1287-1296.
12. a) W. Tückmantel, A. P. Kozikowski, L. J. Romanczyk, J. Am. Chem. Soc. 1999, 121, 12073-12081;
13. b) A. Saito, N. Nakajima, A. Tanaka, M. Ubukata, Tetrahedron 2002, 58, 7829-7837;
14. c) A. P. Kozikowski, W. Tückmantel, G. Böttcher, L. J. Romanczyk, Jr., J. Org. Chem. 2003, 68, 1641-1658;
15. d) A. Saito, N. Nakajima, N. Matsuura, A. Tanaka, M. Ubukata, Heterocycles 2004, 62, 479-489.
16. K. Ohmori, N. Ushimam, K. Suzuki, PNAS 2004, 101, 12002-12007.
17. a) A. Saito, N. Nakajima, A. Tanaka, M. Ubukata, Heterocycles 2003, 61, 287-298;
18. b) A. Saito, N. Nakajima, A. Tanaka, M. Ubukata, Tetrahedron Lett. 2003, 44, 5449-5452.
19. T. A. Geissman, N. N. Yoshimura, Tetrahedron Lett. 1966, 7, 2669-2673.
20. J. G. Sweeny, G. A. Iacobucci, J. Org. Chem. 1979, 44, 2298-2299.
21. a) E. Kiehlmann, N. Lehto, D. Cherniwchan, Can. J. Chem. 1988, 66, 2431-2439;
22. b) H. Kawamoto, N. Tanaka, F. Nakatsubo, K. Murakami, Mokuzai Gakkaishi 1993, 39, 820-824.
23. a) H. Kawamoto, F. Nakatsubo, K. Murakami, J. Wood Chem. Technol. 1990, 10, 59-74;
24. b) H. Kawamoto, F. Nakatsubo, K. Murakami, Mokuzai Gakkaishi 1991, 37, 488-493.
25. S. Buffnoir, Thèse de l'Université de Paris VI, 1998.
26. a) A. K. Ganguli, T. R. Seshadri, F. A. Subramanian, P. Subramanian, Proc. Indian Acad. Sci. 1957, 56, 25-28;
27. b) J. H. Incremona, J. C. Martin, J. Am. Chem. Soc. 1970, 92, 627-631.
28. a) P. J. Steynberg, R. J. J. Nel, H. Van Rensburg, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron 1998, 54, 8153-8158;
29. b) R. W. Hemingway, L. Y. Foo, J. Chem. Soc., Chem. Commun. 1983, 18, 1035-1036.
30. a) M. V. Bhatt, P. T. Perumal, Tetrahedron Lett. 1981, 22, 2605-2608;
31. b) C. H. L. Mouton, J. A. Steenkamp, D. A. Young, B. C. B. Bezuidenhoudt, D. Ferreira, Tetrahedron 1990, 46, 6885-6894;
32. c) M. J. Betts, B. R. Brown, M. R. Shaw, J. Chem. Soc. C 1969, 1178-1184;
33. d) J. A. Steenkamp, D. Ferreira, D. G. Roux, Tetrahedron Lett. 1985, 26, 3045-3048;
34. e) J. A. Steenkamp, C. H. L. Mouton, D. Ferreira, Tetrahedron 1991, 47, 6705-6716.
35. H3H4 coupling constant (2.6 Hz) of the epicatechin derivative 3b does not allow any conclusion concerning the stereochemistry of C4 to be drawn. However, the selective pulse of the H4 proton gave a NOE correlation with H3, but no correlation with H2, while the selective pulse of H3 gave correlations with both H2 and H4 suggesting that H3 would preferably be in an equatorial conformation and that the H4 and H2 protons would be on the opposite side of the C ring, in accordance with an RRS stereochemistry for 3b. Moreover the comparison through molecular modelling (MM3* force field, Monte Carlo style conformational search) of the interproton distances between H2,H3 and H3,H4 with the NOE correlation peak intensity measured for these protons confirmed the S configuration of C4.
36. E. Kiehlmann, N. Lehto, D. Cherniwchan, Can. J. Chem. 1988, 66, 2431-2439.
37. V. Arnaudinaud, B. Nay, S. Verger, A. Nuhrich, G. Deffieux, J. M. Mérillon, J. P. Monti, J. Vercauteren, Tetrahedron Lett. 2001, 42, 5669-5671.
38. A. Saito, Y. Mizushina, H. Ikawa, H. Yoshida, Y. Doi, A. Tanaka, N. Nakajima, Bioorg. Med. Chem. 2005, 13, 2759-2771.
39. K. Barathieu, Ph. D. Thesis, Bordeaux 1 University, 2002, pp. 77-80 (unpublished results).
40. The ratios observed in chloroform for each pair of retomers 9a-d are: 77:23 for B1, 67:33 for B2, 63:37 for B3 and 85:15 for B4.
41. I. Tarascou, K. Barathieu, C. Simon, M. A. Ducasse, Y. André, E. Fouquet, E. J. Dufourc, V. de Freitas, M. Laguerre, I. Pianet, Magn. Reson. Chem. 2006, 44, 868-880.
42. H. K. L. Hundt, D. G. Roux, J. Chem. Soc., Perkin Trans. 1 1981, 1227-1234.
43. A. M. Felix, E. P. Heimer, T. J. Lambros, C. Tzougraki, J. Meienhofer, J. Org. Chem. 1978, 43, 4194-4196.
44. a) H. Sajiki, A. Kume, K. Hattori, K. Hirota, Tetrahedron Lett. 2002, 43, 7247-7250;
45. b) H. Sajiki, A. Kume, K. Hattori, H. Nagase, K. Hirota, Tetrahedron Lett. 2002, 43, 7251-7254.
46. L. J. Romanczyk, A. P. Kozikowski, W. Tückmantel, US Patent, Appl. US 98-169554 19981009, 2002.
47. M. I. Khan, E. Haslan, M. P. Williamson, Magn. Reson. Chem. 1997, 35, 854-858;
48. T. Hatano, R. W. Hemingway, J. Chem. Soc., Perkin Trans. 2 1997, 18, 1035-1043.
49. NMR spectra for 10d were recorded at 5°C in order to avoid the coalescence phenomena observed at 22°C due to the specific rate of rotational isomerization of 10d.