Synthesis of macrocyclic mono- and diolides based on new ω-hydroxyalkadienoic acids with (Z,Z)-1,5-diene moiety

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-07-26 DOI:10.1007/s11172-024-4278-7

I. I. Islamov, I. V. Gaisin, U. M. Dzhemilev, V. A. D’yakonov

引用次数: 0

Abstract

A stereoselective synthesis of new (6Z,10Z)-16-hydroxyhexadeca-6,10-dienoic and (7Z,11Z)-18-hydroxyoctadeca-7,11-dienoic acid that involved the Ti-catalyzed homocyclomagnesiation of the functionally substituted 1,2-dienes was developed. Subsequent intramolecular cyclization of the synthesized ω-hydroxyalkadienoic acids in the presence of catalytic amounts (2.5–10 mol.%) of hafnium(iv) triflate gave unsaturated macrocyclic lactones and diolides with pharmacophoric 1Z,5Z-diene moieties.

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基于具有 (Z,Z)-1,5 二烯分子的新型 ω-hydroxyalkadienoic acids 的大环单二元醇化合物的合成

本研究开发了一种立体选择性合成新的(6Z,10Z)-16-羟基十六碳-6,10-二烯酸和(7Z,11Z)-18-羟基十八碳-7,11-二烯酸的方法，该方法涉及功能取代的 1,2 二烯在钛催化下的均环镁化反应。随后，在催化量（2.5-10 mol.%）的三酸铪存在下，合成的ω-羟基烷二烯酸发生分子内环化反应，产生了具有药效 1Z,5Z-二烯分子的不饱和大环内酯和二元内酯。

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

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.