Epicatechin B-ring conjugates: first enantioselective synthesis and evidence for their occurrence in human biological fluids |
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Authors: | Romanov-Michailidis Fedor Viton Florian Fumeaux René Lévèques Antoine Actis-Goretta Lucas Rein Maarit Williamson Gary Barron Denis |
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Institution: | Nestle Research Center, P.O. Box 44, CH-1000 Lausanne 26, Switzerland. |
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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. |
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