Synthesis of 4.alpha.-arylepicatechins

Details Synthesis of 4.alpha.-arylepicatechins Synthesis of 4.alpha.-arylepicatechins

C - Chemistry, Metallurgy

07

D

C07D 311/62 (2006.01)

Patent

CA 2421513

Oligomeric procyanidins containing 4.alpha.-linked epicatechin units are in nature and have hitherto not been accessible through stereoselective synthesis. Provided herein is the preparation of the prototypical dimer, epicatechin-4.alpha.,8-epicatechin, by reaction of the protected 4-ketones with aryllithium reagents derived by halogen/metal exchange from the aryl bromides. Removal of the 4-hydroxyl group from the resulting tertiary benzylic alcohols is effected by tri-n-butyltin hydride and trifluoroacetic acid in a completely stereoselective manner, resulting in hydride delivery exclusively from the .beta. face.

L'invention concerne des procyanidines oligomériques contenant des unités d'épicatéchine liées en 4.alpha., rares et non accessibles à ce jour par synthèse stéréosélective. L'invention concerne également la préparation du dimère prototypique épicatéchine-4.alpha., 8-épicatéchine par réaction des cétones 4 protégées avec des réactifs d'aryllithium dérivés par échange halogène/métal des bromures d'aryle. L'élimination par l'hydrure tri-n-butyltine et l'acide trifluoroacétique du groupe 4-hydroxyle des alcools benzyliques tertiaires obtenus est entièrement stéréosélective, l'hydrure étant exclusivement délivré de la face .beta..

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