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Paper | Special issue | Vol 79, No. 1, 2009, pp.549-563
Published online, 16th October, 2008
DOI: 10.3987/COM-08-S(D)14
An Efficient Synthesis of Procyanidins Using Equimolar Condensation of Catechin and/or Epicatechin Catalyzed by Ytterbium Triflate

Yoshihiro Mohri, Masayoshi Sagehashi, Taiji Yamada, Yasunao Hattori, Keiji Morimura, Yasunori Hamauzu, Tsunashi Kamo, Mitsuru Hirota, and Hidefumi Makabe*

*Shinshu University, 8304 Minamiminowa-mura, Kamiina-gun, Nagano 399-4598, Japan

Abstract

Stereoselective synthesis of catechin and epicatechin dimers under intermolecular condensation of equimolar amount of catechin derivatives catalyzed by Yb(OTf)3. The coupled products were successfully converted to procyanidins B1, B2, B3, and B4, respectively. Procyanidins B1, B2, B3, and B4 could be used as standard compounds for identifying the polyphenols in natural source.