Thermodynamic Stability of Flavylium Salts as a Valuable Tool to Design the Synthesis of A-Type Proanthocyanidin Analogues

Alfonso Alejo-Armijo, A. Jorge Parola, Fernando Pina, Joaquín Altarejos, Sofía Salido

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A convenient method to synthesize A-type proanthocyanidin analogues from flavylium salts and Ï€-nucleophiles has been developed. It was found that the thermodynamic stability of the starting flavylium salt, assessed by the measurement of the apparent acidity constant (K′a), was the key parameter to design effective one-pot reactions between flavylium salts and nucleophiles such as phloroglucinol and (+)-catechin. When flavylium salts have a pK′a value of 1.7 or lower, the synthesis of the corresponding 2,8-dioxabyciclo[3.3.1]nonane derivative was properly achieved.

Original languageEnglish
Pages (from-to)12297-12304
Number of pages8
JournalJournal of Organic Chemistry
Volume83
Issue number19
DOIs
Publication statusPublished - 5 Oct 2018

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