Total Synthesis of Ellagitannins through Regioselective Sequential Functionalization of Unprotected Glucose

Short total syntheses of natural glycosides (ellagitannins) were performed through sequential and regioselective functionalization of the hydroxy groups of unprotected glucose. The key reactions are β‐selective glycosidation of a gallic acid derivative by using unprotected glucose as a glycosyl dono...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-05, Vol.54 (21), p.6177-6180
Main Authors: Takeuchi, Hironori, Mishiro, Kenji, Ueda, Yoshihiro, Fujimori, Yusuke, Furuta, Takumi, Kawabata, Takeo
Format: Article
Language:English
Subjects:
Catalysts
Derivatives
ellagitannin
Gallic acid
Gallic Acid - chemical synthesis
Gallic Acid - chemistry
Glucose
Glucose - chemical synthesis
Glucose - chemistry
Glucosides
glycosidation
Glycosides
Glycosides - chemical synthesis
Glycosides - chemistry
Glycosylation
Hydrolyzable Tannins - chemical synthesis
Hydrolyzable Tannins - chemistry
organocatalysis
regioselectivity
Stereoisomerism
Sweets
Synthesis
total synthesis
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Summary:Short total syntheses of natural glycosides (ellagitannins) were performed through sequential and regioselective functionalization of the hydroxy groups of unprotected glucose. The key reactions are β‐selective glycosidation of a gallic acid derivative by using unprotected glucose as a glycosyl donor and catalyst‐controlled regioselective introduction of a galloyl group into the inherently less reactive hydroxy group of the glucoside. Short and sweet: Very short total syntheses of ellagitannins were achieved through sequential and regioselective functionalization of the hydroxy groups of unprotected glucose.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201500700