Tetrahedron Letters

Total synthesis of 3, 5-O-dicaffeoylquinic acid and its derivatives

KS Raheem, NP Botting, G Williamson, D Barron

Index: Raheem, K. Saki; Botting, Nigel P.; Williamson, Gary; Barron, Denis Tetrahedron Letters, 2011 , vol. 52, # 52 p. 7175 - 7177

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Citation Number: 6

Abstract

We report the first total synthesis of 3, 5-O-dicaffeoylquinic acid and its derivatives, 3, 5-O- diferuloylquinic acid and 3, 5-(3, 4-dimethoxycinnamyl) quinic acid, in a nine-step sequence. The key step involves Knoevenagel condensations between vanillin, 3, 4- dimethoxybenzaldehyde or 4-hydroxy-3-methoxybenzaldehyde and the dimalonate ester of quinic acid.