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

K. Saki Raheem, Nigel P. Botting, Gary Williamson, Denis Barron

Research output: Contribution to journalArticleResearchpeer-review

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7175-7177
Number of pages3
JournalTetrahedron Letters
Volume52
Issue number52
DOIs
Publication statusPublished - 28 Dec 2011
Externally publishedYes

Keywords

  • Dicaffeoylquinic acids
  • Knoevenagel condensation
  • Metabolism references
  • Natural product synthesis
  • Plant natural products

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