Epicatechin B-Ring Conjugates: First Enantioselective Synthesis and Evidence for Their Occurrence in Human Biological Fluids
2012
Romanov-Michailidis, Fedor | Viton, Florian | Fumeaux, René | Lévèques, Antoine | Actis-Goretta, Lucas | Rein, Maarit | Williamson, Gary | Barron, Denis
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.
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