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Development of an Efficient Synthetic Process for Irisquinone
Synlett ( IF 1.7 ) Pub Date : 2024-02-16 , DOI: 10.1055/s-0042-1751560
Kun Zheng , Qifeng Zhang , Lu Ga , Yuheng Ma , Guodong Liang , Yan Zhao

Irisquinone is a tumor radiotherapy sensitizer and has been found to have broad-spectrum antitumor activity in recent years. The current acquisition method of extracting and purifying from semen irisis has greatly limited its wide application and activity study deeply. In this work an efficient route for the synthesis of the irisquinone was investigated to solve the source of it. The target compound was synthesized by 5-step reactions to Wittig reaction, reduction, oxidation, Wittig reaction, and oxidation using 3,5-dimethoxycarboxaldehyde as the starting material with an overall yield of 48%. The key factors such as the ratio of raw materials, temperatures, solvents, reaction times, and types of base for the main reactions were optimized. In addition, the deprotection and reduction were completed with Pd/C catalytic simultaneously when compound 2 was synthesized from compound 1. In the last reaction, the 3,5-dimethoxybenzene moiety of compound 4 was directly oxidized to 6-methoxy-1,4-benzoquinone by K3[Fe(CN)6]/H2O2 without the need to selectively remove the methyl protecting group, which were the innovative points in the experimental route design of the irisquinone synthesis. This work has opened new perspectives for the artificial synthesis and the development of irisquinone.



中文翻译:

鸢尾醌高效合成工艺的开发

鸢尾醌是一种肿瘤放疗增敏剂,近年来被发现具有广谱抗肿瘤活性。目前从虹膜精液中提取纯化的获取方法极大地限制了其广泛应用和活性研究的深入。在这项工作中,研究了一种有效的鸢尾醌合成路线,以解决其来源问题。以3,5-二甲氧基甲醛为起始原料,经过维蒂希反应、还原、氧化、维蒂希反应、氧化5步反应合成了目标化合物,总收率48%。对主要反应的原料配比、温度、溶剂、反应时间、碱种类等关键因素进行了优化。此外,由化合物1合成化合物2时,在Pd/C催化下同时完成脱保护和还原反应。在最后的反应中,化合物4的3,5-二甲氧基苯部分被K 3 [Fe(CN) 6 ]/H 2 O 2直接氧化为6-甲氧基-1,4-苯醌,无需选择性去除甲基保护基团是鸢尾醌合成实验路线设计的创新点。该工作为鸢尾醌的人工合成和开发开辟了新的视角。

更新日期:2024-02-17
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