An efficient synthesis of procyanidins using equimolar condensation of catechin and/or epicatechin catalyzed by ytterbium triflate

Heterocycles

Volumn 79, Issue C, 2009, Pages 549-563

  Mohri, Yoshihiro ^a   Sagehashi, Masayoshi ^a   Yamada, Taiji ^a   Hattori, Yasunao ^a   Morimura, Keiji ^a,b   Hamauzu, Yasunori ^a   Kamo, Tsunashi ^a   Hirota, Mitsuru ^a   Makabe, Hidefumi ^a  

^a SHINSHU UNIVERSITY   (Japan)

^b Geol Chemical Co Ltd   (Japan)

Author keywords

Antioxidant; Condensation; Lewis Acid; Polyphenol; Rare Metal

Indexed keywords

EID: 67651099112     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(D)14     Document Type: Article

References (21)

1. Ferreira D., and Li X.-C. Nat. Prod. Rep. 17 (2000) 193
2. Ferreira D., and Li X.-C. Nat. Prod. Rep. 19 (2002) 517
3. Corder R., Muller W., Khan N.Q., Marks S.C., Wood E.G., Carrier M.J., and Crozier A. Nature 444 (2006) 566
4. Tückmantel W., Kozikowski A.P., and Romanczyk Jr. L.J. J. Am. Chem. Soc. 121 (1999) 12073
5. Saito A., Nakajima N., Tanaka A., and Ubukata M. Tetrahedron 58 (2002) 7829
6. Kozikowski A.P., Tückmantel W., Böttcher G., and Romanczyk Jr. L.J. J. Org. Chem. 68 (2003) 1641
7. Saito A., Nakajima N., Matsuura N., Tanaka A., and Ubukata M. Heterocycles 62 (2004) 479
8. Oyama K.-I., Kuwano M., Ito M., Yoshida K., and Kondo T. Tetrahedron Lett. 49 (2008) 3176
9. Kozikowski A.P., Tückmantel W., and Hu Y. J. Org. Chem. 66 (2001) 1287
10. Saito A., Nakajima N., Tanaka A., and Ubukata M. Heterocycles 61 (2003) 287
11. Saito A., Nakajima N., Tanaka A., and Ubukata M. Tetrahedron Lett. 44 (2003) 5449
12. Tarascou I., Barathieu K., Andé Y., Pianet I., Dufourc E.J., and Fouquet E. Eur. J. Org. Chem. (2006) 5367
13. For preliminary communication. Mohri Y., Sagehashi M., Yamada T., Hattori Y., Morimura K., Kamo T., Hirota M., and Makabe H. Tetrahedron Lett. 48 (2007) 5891
14. Kawamoto H., Nakatsubo F., and Murakami K. Mokuzai Gakkaishi 37 (1991) 488
15. Saito A., Nakajima N., Tanaka A., and Ubukata M. Biosci. Biotechnol. Biochem. 66 (2002) 1764
16. 4 mediated oxidative condensation of tetra-O-methyl-3-oxo-catechin with tetra-O-methylcatechin. Matthew A.C., Bonnet S.L., and van der Westhuizen J.H. Org. Lett. 10 (2008) 3865
17. Ohomori K., Ushimaru N., and Suzuki K. Proc. Nat. Acad. Sci. USA 101 (2004) 12002
18. Hayes C.J., Whittaker B.P., Watson S.A., and Grabowska A.M. J. Org. Chem. 71 (2006) 9701
19. 13C-NMR data of 1 and 2 were not described in ref. 4d and 6a. It may be due to the broadening of the signals.
20. Hamauzu Y., Irie M., Kondo M., and Fujita T. Food Chem. 108 (2008) 488
21. B.-J. Xie and co-workers reported that procyanidin B2 was also identified as a major constituent of procyanidin dimer by HPLC analysis in Granny Smith apple. Xiao J.-S., Liu L., Wu H., Xie B.-J., Yang E.-N., and Sun Z.-D. J. Agric. Food Chem. 56 (2008) 2096