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Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives
Authors:K Saki Raheem  Nigel P Botting  Gary WilliamsonDenis Barron
Institution:a School of Chemistry, University of St. Andrews, KY16 9ST Scotland, UK
b Nestle Research Center, PO Box 44, CH-1000, Lausanne 26, Switzerland
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.
Keywords:Dicaffeoylquinic acids  Natural product synthesis  Knoevenagel condensation  Metabolism references  Plant natural products
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