Isolation of key intermediates during formation of oolongtheanins

Oolongtheanin-3′-O-gallate (2b) was obtained by treatment of (−)-EGCg (1d) with CuCl2. This transformation was achieved over three steps, with the isolation of two intermediates; their chemical structures were determined through derivatization reactions, MS, and 1D/2D NMR techniques. One intermediat...

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Bibliographic Details
Published inTetrahedron letters Vol. 54; no. 51; pp. 7040 - 7043
Main Authors Hirose, Sayumi, Tomatsu, Kaoru, Yanase, Emiko
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.12.2013
Elsevier
Subjects
Catechin
Chemistry
Chemistry, Organic
Dimers
Formations
Heating
Nuclear magnetic resonance
Oolong tea
Oolongtheanin-3′-O-gallate
Physical Sciences
Pro-oolongtheanin-3′-O-gallate
Science & Technology
Solvents
Tetrahedrons
Transformations
Two dimensional
Pro-oolongtheanin-3′-O-gallate
Catechin
Oolong tea
Oolongtheanin-3′-O-gallate
OXIDATION
Pro-oolongtheanin-3 '-O-gallate
MECHANISM
TANNINS
CATECHINS
IDENTIFICATION
POLYPHENOLS
BLACK TEA
EPIGALLOCATECHIN GALLATE
THEASINENSIN
Oolongtheanin-3 '-O-gallate
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Summary:Oolongtheanin-3′-O-gallate (2b) was obtained by treatment of (−)-EGCg (1d) with CuCl2. This transformation was achieved over three steps, with the isolation of two intermediates; their chemical structures were determined through derivatization reactions, MS, and 1D/2D NMR techniques. One intermediate was identified as dehydrotheasinensin A (3); the other was identified as the novel dimer pro-oolongtheanin-3′-O-gallate (6). Compound 3 was converted to 6 by heating in aprotic solvent, and compound 6 was converted to 2b by addition of water.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.10.069