一种异喹啉类生物碱小檗碱、黄连碱和吴茱萸碱的统一合成策略。
A Unified Strategy for the Syntheses of the Isoquinolinium Alkaloids Berberine, Coptisine, and Jatrorrhizine.
机构信息
Department of Chemistry , The University of Kansas , 2010 Malott Hall, 1251 Wescoe Hall Drive , Lawrence , Kansas 66045 , United States.
出版信息
Org Lett. 2018 Jul 20;20(14):4281-4284. doi: 10.1021/acs.orglett.8b01702. Epub 2018 Jun 28.
Abstract
Total syntheses of the antibacterial alkaloids berberine, coptisine, and jatrorrhizine have been achieved in four steps through a unified route. The key step of this strategy is an efficient intramolecular Friedel-Crafts alkoxyalkylation which, following oxidation, establishes the isoquinolinium core of these natural products. Herein, the design and development of this synthetic strategy, which has enabled the shortest and most efficient syntheses of these alkaloids reported to date, is described.
摘要
通过统一的路线，已经实现了抗菌生物碱小檗碱、黄连碱和防己诺林碱的全合成，共四步。该策略的关键步骤是高效的分子内傅克烷氧基烷基化反应，该反应在氧化后构建了这些天然产物的异喹啉核心。本文描述了该合成策略的设计和开发，该策略实现了迄今为止这些生物碱最短和最高效的合成。
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