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

Raheem, S., Botting, Nigel P., Williamson, G. and Barron, D. 2011. Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives. Tetrahedron Letters. 52 (52), p. 7175. https://doi.org/10.1016/j.tetlet.2011.10.127

TitleTotal synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives
AuthorsRaheem, S., Botting, Nigel P., Williamson, G. and Barron, D.
Abstract

We report the first total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives, 3,5-O-diferuloylqui- nic 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-methoxy- benzaldehyde and the dimalonate ester of quinic acid.

KeywordsDicaffeoylquinic acids, Natural product synthesis, Knoevenagel condensation, Metabolism references, Plant natural products
JournalTetrahedron Letters
Journal citation52 (52), p. 7175
ISSN0040-4039
Year2011
PublisherElsevier
Digital Object Identifier (DOI)https://doi.org/10.1016/j.tetlet.2011.10.127
Publication dates
Published online28 Oct 2011
Published in print28 Dec 2011

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