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

被引：10

作者：

Alejo-Armijo, Alfonso ^{[1
,2
]}

Jorge Parola, A. ^{[2
]}

Pina, Fernando ^{[2
]}

Altarejos, Joaquin ^{[1
]}

Salido, Sofia ^{[1
]}

机构：

[1] Univ Jaen, Dept Quim Inorgan & Organ, Fac Ciencias Expt, Campus Excelencia Int Agroalimentario,CeiA3, Jaen 23071, Spain

[2] Univ Nova Lisboa, Dept Quim, Fac Ciencias & Tecnol, LAQV,REQUIMTE, P-2829516 Caparica, Portugal

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

关键词：

CINNAMTANNIN B-1; BAY WOOD; STEREOSELECTIVE-SYNTHESIS;

D O I：

10.1021/acs.joc.8b01780

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient method to synthesize A-type proanthocyanidin analogues from flavylium salts and pi-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.

引用

页码：12297 / 12304

页数：8

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