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Bioinspired Total Synthesis of (−)‐Vescalin: A Nonahydroxytriphenoylated C ‐Glucosidic Ellagitannin
Author(s) -
Richieu Antoine,
Peixoto Philippe A.,
Pouységu Laurent,
Deffieux Denis,
Quideau Stéphane
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201707613
Subject(s) - ellagitannin , hemiacetal , aldol reaction , stereochemistry , total synthesis , wittig reaction , chemistry , sequence (biology) , biogenesis , ring (chemistry) , organic chemistry , polyphenol , biochemistry , antioxidant , gene , catalysis
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.