Epicatechin B-ring conjugates: First enantioselective synthesis and evidence for their occurrence in human biological fluids

Fedor Romanov-Michailidis, Florian Viton, René Fumeaux, Antoine Lévèques, Lucas Actis-Goretta, Maarit Rein, Gary Williamson, Denis Barron

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19 Citations (Scopus)

Abstract

Herein, the first enantioselective total synthesis of a number of biologically relevant (-)-epicatechin conjugates is described. The success of this synthesis relied on (i) optimized conditions for the stereospecific cyclization step leading to the catechin C ring; on (ii) efficient conjugation reactions; and on (iii) optimized deprotection sequences. These standard compounds have been subsequently used to elucidate for the first time the pattern of (-)-epicatechin conjugates present in four different human biological fluids following (-)-epicatechin absorption.

Original languageEnglish
Pages (from-to)3902-3905
Number of pages4
JournalOrganic Letters
Volume14
Issue number15
DOIs
Publication statusPublished - 3 Aug 2012
Externally publishedYes

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