From Pseudocyclic to Macrocyclic Ionophores: Strategies toward the Synthesis of Cyclic Monensin Derivatives

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC
Michał Sulik, Robert Graniczny, Jan Janczak, Dagmara Kłopotowska, Joanna Wietrzyk, Adam Huczyński
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引用次数: 0

Abstract

There has been a long search for a simple preparation of new cyclic analogues of ionophore antibiotics. We report a simple and general synthesis of three new cyclic derivatives of polyether ionophore, monensin A (MON). The application of the Huisgen 1,3-dipolar cycloaddition of azides and terminal alkynes to macrocyclization results in a concise, synthetic route to monensin lacton or lactam in only 4 steps. Additionally, macrolactamization by a simple amidation reaction using HATU, a commonly used conjugating agent, gives 72% yields and utilizes neither high dilution techniques nor template effects in the cyclization step. This in turn enables ready access to a range of unnatural MON analogues, showing the ability to form complexes with monovalent and divalent metal cations.

Abstract Image

从伪环到大环离子载体:环状莫能菌素衍生物的合成策略
长期以来,人们一直在寻找一种新的离子载体抗生素环类似物的简单制备方法。本文报道了聚醚离子载体三种新的环状衍生物莫能菌素a (MON)的简单合成。应用Huisgen 1,3-偶极环加成叠氮化物和末端炔进行大环化,只需4步即可合成莫能菌素内酯或内酰胺。此外,使用常用的偶联剂HATU进行简单的酰胺化反应进行大内酰胺化,产率为72%,并且在环化步骤中既不使用高稀释技术也不使用模板效应。这反过来又使得可以随时获得一系列非天然的MON类似物,显示出与一价和二价金属阳离子形成配合物的能力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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