Synthesis of procyanidins by stepwise- and self-condensation using 3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3′,4′-tetra-O-ben zyl-(+)-catechin and (-)-epicatechin as a key building monomer

Tetrahedron Letters

Volumn 49, Issue 19, 2008, Pages 3176-3180

  Oyama, Kin ichi ^a   Kuwano, Miyuki ^a   Ito, Mie ^a   Yoshida, Kumi ^a   Kondo, Tadao ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

4 Acetoxy 3 acetylcatechin; 4 Acetoxy 3 acetylepicatechin; Procyanidin; Stepwise and self condensation

Indexed keywords

3,4 4 ACETOXY 3 O ACETYL 4 DEHYDRO 5,7,3',4' TETRA O BENZYL CATECHIN; 4 ACETOXY 3 ACETYLCATECHIN; 4 ACETOXY 3 ACETYLEPICATECHIN; 5,7,3',4' TETRA O BENZYLOXYFLAVAN 3 OL; CATECHIN; EPICATECHIN; FLAVAN DERIVATIVE; MONOMER; PROCYANIDIN DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; BIOMASS; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENOLYSIS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; POLYMERIZATION; STEREOCHEMISTRY; STEREOSPECIFICITY;

TETRA;

EID: 41849117233     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.173     Document Type: Article

References (43)

1. Haslam E. Practical Polyphenolics (1998), Cambridge University Press
2. Rice-Evans C.A., Miller N.J., and Paganga G. Free Radical Biol. Med. 20 (1996) 933-956
3. Harborne J.B., and Williams C.A. Phytochemistry 55 (2000) 481-504
4. Ferreira D., and Li X.-C. Nat. Prod. Rep. 17 (2000) 193-212
5. Middleton Jr. E. Pharmacol. Rev. 52 (2000) 673-751
6. Mackenzie G.G., Carrasquedo F., Delfino J.M., Keen C.L., Fraga C.G., and Oteiza P.I. FASEB J. 18 (2004) 167-169
7. 2a,3:. Hammerstone J.F., Lazarus S.A., Mitchell A.E., Rucker R., and Schmitz H.H. J. Agric. Food Chem. 47 (1999) 490-496
8. Yang Y., and Chien M. J. Agric. Food Chem. 48 (2000) 3990-3996
9. Wollgast J., Pallaroni L., Agazzi M.-E., and Anklam E. J. Chromatogr., A 926 (2001) 211-220
10. Es-Safi N.-E., Guyot S., and Ducrot P.-H. J. Agric. Food Chem. 54 (2006) 6969-6977
11. Ariga T., and Asao Y. Agric. Biol. Chem. 45 (1981) 2709-2712
12. Ariga T., Koshiyama I., and Fukushima D. Agric. Biol. Chem. 55 (1988) 2717-2722
13. Yoshida K., Kondo T., Ito M., and Kondo T. ITE Lett. 6 (2005) 19-24
14. Our unpublished result: The procyanidin oligomers (up to 13-mer) were observed in the extract from red adzuki seed coat (Vigna angularis) by ESI-Q-TOF MS.
15. Kawamoto H., Nakatsubo F., and Murakami K. Mokuzai Gakkaishi. 37 (1991) 488-493
16. Tückmantel W., Kozikowski A.P., and Romanczyk Jr. L.J. J. Am. Chem. Soc. 121 (1999) 12073-12081
17. Kozikowski A.P., Tückmantel W., Böttcher G., and Romanczyk Jr. L.J. J. Org. Chem. 65 (2000) 5371-5381
18. Arnaudinaud V., Nay B., Nuhrich A., Deffieux G., Mérillon J.-M., Monti J.-P., and Vercauteren J. Tetrahedron Lett. 42 (2001) 1279-1281
19. Kozikowski A.P., Tückmantel W., and Hu Y. J. Org. Chem. 66 (2001) 1287-1296
20. Saito A., Nakajima N., Tanaka A., and Ubukata M. Biosci. Biotechnol. Biochem. 66 (2002) 1764-1767
21. Saito A., Nakajima N., Tanaka A., and Ubukata M. Tetrahedron 58 (2002) 7829-7837
22. Saito A., Tanaka A., Ubukata M., and Nakajima N. Synlett (2004) 1069-1073
23. Ohmori K., Ushimaru N., and Suzuki K. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 12002-12007
24. Saito A., Doi Y., Tanaka A., Matsuura N., Ubukata M., and Nakajima N. Bioorg. Med. Chem. 12 (2004) 4783-4790
25. Mohri Y., Sagehashi M., Yamada T., Hattori Y., Morimura K., Kamo T., Hirota M., and Makabe H. Tetrahedron Lett. 48 (2007) 5891-5894
26. Kawamoto H., Nakatsubo F., and Murakami K. J. Wood. Chem. Technol. 10 (1990) 59-74
27. Yoneda S., Kawamoto H., and Nakatsubo F. J. Chem. Soc., Perkin Trans. 1 (1997) 1025-1030
28. Ushimaru, N.; Ohmori, K.; Suzuki, K. The abstract of the 79th spring meetings (The Chemical Society of Japan) 2001, 1073.
29. Ohmori K., Ushimaru N., and Suzuki K. Tetrahedron Lett. 43 (2002) 7753-7756
30. Ohmori K., Hatakeyama K., Ohrui H., and Suzuki K. Tetrahedron 60 (2004) 1365-1373
31. N1-like reaction.
32. Nakamura S., Oyama K.-I., Kondo T., and Yoshida K. Heterocycles 73 (2007) 451-460
33. 3,4 = 1.4 Hz).
34. 7b
35. 1.5 equiv of 4a to 2 was used. The reaction temperature was raised gradually from -78 °C to -10 °C. The products were decomposed at rt in the reaction mixture.
36. After acetylation, the structural identification was performed by various 1D and 2D (COSY, NOESY, HMQC, and HMBC) NMR experiments.
37. 5f,g
38. 5k
39. A long reaction time with a large amount of Pd catalyst lowered the yield because of cleavage of interflavan bonds.
40. To prevent cleavage of interflavan bonds, partial hydrogenolysis followed by acetylation was conducted repeatedly.
41. See Supplementary data.
42. 3
43. 6b