Protecting-Group-Free Solid-Phase Anchoring of Polyphenolic C-Glucosidic Ellagitannins and Synthesis of 1-Alkylamino-Vescalagin Derivatives

• Published in: European journal of organic chemistry Vol. 2014; no. 23; pp. 4963 - 4972
• Main Authors: Douat, Céline, Berni, Emanuela, Jacquet, Rémi, Pouységu, Laurent, Deffieux, Denis, Quideau, Stéphane
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.08.2014; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Amines; Chemistry; Chemistry, Organic; Ellagitannins; Natural products; Physical Sciences; Polyphenols; Science & Technology; Solid-phase synthesis; HYDROLYZABLE TANNINS; Amines; GLYCOSIDIC ELLAGITANNINS; CHESTNUT; CASTALAGIN; Solid-phase synthesis; VESCALAGIN; Ellagitannins; Natural products; Polyphenols; CHEMISTRY; HIGH-RESOLUTION H-1-NMR; INHIBITOR; THIOETHERS; SULFENYL CHLORIDES
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201402444

The C‐glucosidic ellagitannins vescalagin and vescalin are among the plant polyphenols that have been shown to interact with protein targets in a specific manner. This work describes a protecting‐group‐free method to immobilize these protein‐binding natural products on a solid support, and a functionalizing cleavage method, which is adaptable to the solution‐phase synthesis of vescal(ag)in derivatives, and which advantageously permitted the preparation of 1‐alkylamino derivatives of vescalagin. A protecting‐group‐free method immobilizes the protein‐binding polyphenolic C‐glucosidic ellagitannin vescalagin on a solid support. A functionalizing resin‐cleavage method introduces amino groups at the C‐1 position of the vescalagin core, and its adaptation to liquid‐phase conditions offers convenient chemo‐ and stereoselective access to 1‐alkylamino‐vescalagin derivatives in good yields.