First and biomimetic total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A.
The first total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A, was accomplished by relying on a biomimetic aldol-type formation of its characteristic C-aryl glucosidic bond through the exploitation of the inherent chemical reactivity of a glucopyranosic hemiacetal precursor.
Université de Bordeaux, Institut des Sciences Moléculaires (CNRS-UMR 5255), Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex, France.
Denis
D
Deffieux
Anna
A
Natangelo
Gaëlle
G
Malik
Laurent
L
Pouységu
Jaime
J
Charris
Stéphane
S
Quideau
D032701:Biomimetics; D006576:Heterocyclic Compounds, 4 or More Rings; D047348:Hydrolyzable Tannins / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
C557991:5-O-desgalloylepipunicacortein A; D006576:Heterocyclic Compounds, 4 or More Rings; D047348:Hydrolyzable Tannins