Open AccessSynthetic Studies of Proanthocyanidins. Highly Stereoselective Synthesis of the Catechin Dimer, Procyanidin-B3
Author(s) -
Akiko Saito,
Noriyuki Nakajima,
Akira Tanaka,
Makoto Ubukata
Publication year - 2002
Publication title -
bioscience biotechnology and biochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.509
H-Index - 116
eISSN - 1347-6947
pISSN - 0916-8451
DOI - 10.1271/bbb.66.1764
Subject(s) - proanthocyanidin , catechin , chemistry , dimer , stereoselectivity , polyphenol , stereochemistry , organic chemistry , catalysis , antioxidant
A stereoselective synthesis of benzylated procyanidin-B3, a condensed catechin dimer, is described. Condensation of 5,7,3',4'-tetrabenzylcatechin with (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan as an electrophile in the presence of TiCl4 led to octabenzylated procyanidin-B3 stereoselectively.
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