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■ Condensation of Catechin and Epicatechin Incorporating a TBS-Protecting Group

Noriyuki Nakajima,* Keiko Horikawa, Norimasa Takekawa, Masahiro Hamada, and Takao Kishimoto

*Biotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Kosugi, Toyama 939-0398, Japan

Abstract

Stereoselective synthesis of catechin and epicatechin dimers incorporating a tert-butyldimethylsilyl (TBS)-protecting group under intermolecular condensation is achieved using SnCl4 as the Lewis acid. Four TBS-protected dimers were successfully converted to the deca-acetates of procyanidin B1, B2, B3, and B4 easily via the TBS-deprotection process. This procedure offers an advantage for dimmer synthesis in large-scale over existing benzyl-protecting methods.