Synlett 2006(17): 2827-2829  
DOI: 10.1055/s-2006-950283
LETTER
© Georg Thieme Verlag Stuttgart · New York

An Efficient Synthesis of (±)-Epigallocatechin Gallate by Reductive ­Intramolecular Etherification

Makoto Kitade, Yoshiaki Ohno, Hiroshi Tanaka, Takashi Takahashi*
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-S1-35 Ookayama, Meguro, Tokyo 152-8552, Japan
Fax: +81(3)57342120; e-Mail: ttak@apc.titech.ac.jp;
Further Information

Publication History

Received 21 June 2006
Publication Date:
09 October 2006 (online)

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Abstract

The synthesis of (±)-epigallocatechin gallate by direct cyclization to the cis-3-acyloxy-2-arylbenzopyranee is described. α-Acyloxylketones, possessing a 2-hydroxylphenyl group at the β-position, underwent intramolecular reductive etherification to give cis-3-acyloxy-2-arylbenzopyran due to neighboring group participation of the acyloxyl group at the α-position. Using this method, we accomplished the stereoselective synthesis of (±)-epigallo­catechin gallate.