Bioinspired Total Synthesis of (−)‐Vescalin: A Nonahydroxytriphenoylated  C ‐Glucosidic Ellagitannin | Zendy

Richieu Antoine | Zendy; Peixoto Philippe A. | Zendy; Pouységu Laurent | Zendy; Deffieux Denis | Zendy; Quideau Stéphane | Zendy

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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.

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