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Total Synthesis of Cercidinin A
Author(s) -
Yamada Hidetoshi,
Ohara Kenya,
Ogura Takahito
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301219
Subject(s) - ellagitannin , chemistry , moiety , intramolecular force , total synthesis , stereochemistry , diol , synthon , organic chemistry , combinatorial chemistry , polyphenol , antioxidant
An ellagitannin, cercidinin A, was synthesized through both intramolecular coupling of gallates on a glucose moiety and double esterification of protected hexahydroxydiphenic acid to a diol. The total synthesis confirmed the revised structure of cercidinin A as 1,2,6‐tri‐ O ‐galloyl‐3,4‐( R )‐hexahydroxydiphenoyl (HHDP) β‐ D ‐glucose. This is the first synthesis of 3,4‐HHDP‐bridged ellagitannins and was achieved after overcoming two challenges: (1) full galloylation of β‐glucose hindered the formation of the 3,4‐HHDP group, and (2) the fully benzylated galloyl group, which is a routine component in ellagitannin synthesis, was not always appropriate. The solutions to these problems can be used to form a strategy for the synthesis of complex ellagitannins.