4 years ago

Bioinspired Total Synthesis of (−)-Vescalin: A Nonahydroxytriphenoylated C-Glucosidic Ellagitannin

Bioinspired Total Synthesis of (−)-Vescalin: A Nonahydroxytriphenoylated C-Glucosidic Ellagitannin
Stéphane Quideau, Denis Deffieux, Philippe A. Peixoto, Laurent Pouységu, Antoine Richieu
The first total synthesis of the 2,3,5-O-(S,R)-nonahydroxytriphenoylated (NHTP) C-glucosidic ellagitannin (−)-vescalin was accomplished through a series of transformations mimicking the sequence of events leading to its biogenesis. The key steps of this synthesis encompass a Wittig-mediated ring opening of a glucopyranosic hemiacetal, a C-glucosidation event through a phenolic aldol-type reaction, and a Wynberg–Feringa–Yamada-type oxidative phenolic coupling, which forged the NHTP unit of (−)-vescalin. Catch a tan(nin): The total synthesis of a first member of the nonahydroxytriphenoylated (NHTP) C-glucosidic ellagitannins, (−)-vescalin, is described. The route is closely tailored to the commonly proposed sequence of events leading to its biogenesis. Its characteristic 2,3,5-(S,R)-NHTP unit was elaborated by a copper(II)-mediated Wynberg–Feringa–Yamada-type phenolic coupling using the achiral bicyclic diamine N,N′-dimethylbispidine.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707613

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