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Electrooxidative Dearomatization to Spiroisoxazolines: Application to Total Synthesis of Xanthoisoxazoline B
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2021-10-28 , DOI: 10.1002/adsc.202101062
Dengfeng Chen 1 , Tianyu He 2 , Yongcan Jin 2 , Shenlin Huang 2
Affiliation  

The synthesis of spiroisoxazoline molecules has been developed via anodic oxidative dearomatization of 4-methoxybenzyl oximes. The reaction is thought to proceed through 5-exo C−O bond-forming cyclization of oxime radicals with arenes on the basis of cyclic voltammetry studies. Moreover, spiroisoxazolines can be built directly from readily available carbonyl tethered phenolics via an oximation/dearomatization cascade. Using this spiroisoxazolization as the key step, the first total synthesis of xanthoisoxazoline B has been achieved in three steps.

中文翻译:

螺异恶唑啉的电氧化脱芳构化:在黄硫异恶唑啉 B 的全合成中的应用

已通过 4-甲氧基苄基肟的阳极氧化脱芳构化开发了螺异恶唑啉分子的合成。根据循环伏安法研究,该反应被认为是通过肟自由基与芳烃的 5 - exo CO-O 键环化来进行的。此外,螺异恶唑啉可以通过肟化/脱芳构化级联直接由容易获得的羰基束缚酚醛树脂构建。以这种螺异恶唑化为关键步骤,黄硫异恶唑啉 B 的首次全合成分三步完成。
更新日期:2021-10-28
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