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使用游离黄烷单元作为亲核试剂合成双链接原花青素:环合高区域选择性的起源探讨。

Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation.

机构信息

Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.

出版信息

Org Biomol Chem. 2019 Oct 23;17(41):9129-9134. doi: 10.1039/c9ob01896d.

DOI:10.1039/c9ob01896d
PMID:31584055
Abstract

A synthesis method of doubly linked flavan dimers is reported via the acid-promoted annulation reaction using nascent catechins, (+)-catechin or (-)-epicatechin, as a dianionic partner and an ethylenedioxy-bridged flavan as a dicationic partner. Procyanidins A1 and A2 were synthesized. On the high regioselectivity of the annulation reactions, model experiments and computational studies were carried out.

摘要

本文报道了一种通过酸促进的芳构化反应合成双链接二氢黄酮的方法,该方法使用新生儿儿茶素(+)-儿茶素或(-)-表儿茶素作为二阴离子体,乙二氧基桥连二氢黄酮作为二阳离子体。合成了原花青素 A1 和 A2。对芳构化反应的高区域选择性进行了模型实验和计算研究。

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Angew Chem Int Ed Engl. 2022 Jul 11;61(28):e202205106. doi: 10.1002/anie.202205106. Epub 2022 May 20.
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