Synthesis 2016; 48(10): 1525-1532
DOI: 10.1055/s-0035-1561390
paper
© Georg Thieme Verlag Stuttgart · New York

Concise Synthesis of Cinnamtannin A2 from Dimeric Epicatechin Electrophile and Nucleophile Prepared by Zn(OTf)2-Mediated Self-Condensation

Mikihiro Ichikawa ◊
a   Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan
,
Kohki Takanashi ◊
a   Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan
,
Manato Suda ◊
a   Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan
,
Yasunao Hattori
b   Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan
,
Sei-ichi Kawahara
c   St. Cousair Co., Ltd., 1260 Imogawa, Kami-minochi, Iizuna, Nagano, 389-1201, Japan
,
Hiroshi Fujii
d   Department of Interdisciplinary Genome Sciences and Cell Metabolism, Institute for Biomedical Sciences, Interdisciplinary Cluster for Cutting Edge Research, Shinshu University, Minami-minowa, Kami-ina, Nagano, 399-4598, Japan   Email: makabeh@shinshu-u.ac.jp
,
Hidefumi Makabe*
a   Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan
d   Department of Interdisciplinary Genome Sciences and Cell Metabolism, Institute for Biomedical Sciences, Interdisciplinary Cluster for Cutting Edge Research, Shinshu University, Minami-minowa, Kami-ina, Nagano, 399-4598, Japan   Email: makabeh@shinshu-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 04 January 2016

Accepted after revision: 23 January 2016

Publication Date:
25 February 2016 (online)


◊ These authors contributed equally

Abstract

The synthesis of cinnamtannin A2 from dimeric epicatechin nucleophile and electrophile was accomplished. Dimeric epicatechin nucleophile was prepared directly by reduction of the C-4′′ 1-ethoxy­ethoxy group of the electrophile which was previously synthesized by us.

Supporting Information