Galloyl-derived orthoquinones as reactive partners in nucleophilic additions and Diels-Alder dimerizations: A novel route to the dehydrodigalloyl linker unit of agrimoniin-type ellagitannins

被引：59

作者：

Feldman, KS ^{[1
]}

Quideau, S ^{[1
]}

Appel, HM ^{[1
]}

机构：

[1] PENN STATE UNIV, PESTICIDE RES LAB, UNIVERSITY PK, PA 16802 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 19期

关键词：

D O I：

10.1021/jo961043u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

引用

页码：6656 / 6665

页数：10

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