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Enantioselective synthesis of orthogonally protected (2R,3R)-(−)-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (−)-epicatechin glucuronides and sulfates.

Date Published: 
Monday, April 15, 2013

Tetrahedron: Asymmetry 2013, 24 (7), 362-373.

Zhang, M.; Erik Jagdmann Jr, G.; Van Zandt, M.; Beckett, P.; Schroeter, H.

Ten orthogonally protected (−)-epicatechin and 3′- or 4′-O-methyl-(−)-epicatechin derivatives were prepared in a regiospecific and enantioselective manner. For each orthogonally protected (−)-epicatechin derivative, one specific phenolic hydroxyl was protected with a methoxymethyl (MOM) or p-methoxybenyzl (PMB) group and the remainder were protected as benzyl ethers. These uniquely protected (−)-epicatechin derivatives were designed to facilitate the regiospecific installation of a glucuronic acid or sulfate unit onto (−)-epicatechin after selective removal of the MOM or PMB protecting group to provide authentic standards of (−)-epicatechin glucuronides and sulfates.