Work

Total Synthesis of (−)‐Vescalagin, the Iconic Member of the C ‐Glucosidic Ellagitannin Family

Year: 2025

Type: article

Abstract: The first total synthesis of the 2,3,5-O-(S,R)-NonaHydroxyTriPhenoylated (NHTP) and 4,6-O-(S)-HexaHydroxy-DiPhenoylated (HHDP) C-glucosidic ellagitannin (-)-vescalagin was accomplished through a bioinspired route involving intramolecular atroposelective cupric-diamine complex-mediated phenolic couplings of gallates to forge its HHDP and NHTP units and a methoxyamine-driven opening of a glucopyranose intermediate followed by a phenolic aldol-type reaction to form its C-arylglucosidic bond. The minor epimer that resulted from this bond-forming event was used to complete also a first total synthesis of the vescalagin epimer, (-)-castalagin.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202501159

Authors: Romain Larrieu, Anaëlle Cornu, Laurent Pouységu, Denis Deffieux, Stéphane Quideau

Institutions: Centre National de la Recherche Scientifique, Université de Bordeaux, Institut des Sciences Moléculaires

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,640

Funders: Ministère de l'Enseignement supérieur, de la Recherche et de l'Innovation, Centre National de la Recherche Scientifique, Institut Universitaire de France