Chemical Communications 2012-08-28

A new synthetic strategy for catechin-class polyphenols: concise synthesis of (-)-epicatechin and its 3-O-gallate.

Sven Stadlbauer, Ken Ohmori, Fumihiko Hattori, Keisuke Suzuki

Index: Chem. Commun. (Camb.) 48(67) , 8425-7, (2012)

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Abstract

Concise synthesis of (-)-epicatechin and its 3-O-gallate is described, illustrating efficacy of the new strategy for catechin-class polyphenols based on assembly of lithiated fluorobenzene and epoxy alcohol followed by a pyran cyclization. 1,3,5-Trifluorobenzene serves as the A-ring equivalent for functionalization and the pyran annulation.