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Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives |
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| Authors: | K. Saki Raheem Nigel P. Botting Gary WilliamsonDenis Barron |
| Affiliation: | 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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