Electrophilic Cyclization and Intermolecular Acetalation of 2-(4-Hydroxybut-1-yn-1-yl)benzaldehydes: Synthesis of Diiodinated Diepoxydibenzo[c,k][1,9]dioxacyclohexadecines,The Journal of Organic Chemistry

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Electrophilic Cyclization and Intermolecular Acetalation of 2-(4-Hydroxybut-1-yn-1-yl)benzaldehydes: Synthesis of Diiodinated Diepoxydibenzo[c,k][1,9]dioxacyclohexadecines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-09-08 00:00:00 , DOI: 10.1021/acs.joc.7b01646
Jia Wang ₁ , Hai-Tao Zhu ₂ , Si Chen ₁ , Cheng Luan ₁ , Yu Xia ₁ , Yi Shen ₁ , Ying-Xiu Li ₁ , Yingxi Hua ₁ , Yong-Min Liang ₁

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An expedient strategy for the preparation of diiodinated diepoxydibenzo[c,k][1,9]dioxacyclohexadecines from readily available 2-(4-hydroxybut-1-yn-1-yl)benzaldehydes through electrophile-triggered tandem cyclization/intermolecular acetalation sequence has been presented. The electrophilic macrocyclization can be performed under mild conditions and in up to gram quantities. Moreover, palladium-catalyzed coupling and reduction reactions of the resulting iodides could efficiently afford oxa-macrocycles.

中文翻译：

2-（4-羟基丁-1-yn-1-基）苯甲醛的亲电环化和分子间缩醛反应：二碘代二环氧二苯并[ c，k ] [1,9]二氧杂环十六烷的合成

通过亲电触发的串联环化/分子间缩醛序列从易得的2-（4-羟基丁-1-yn-1-基）苯甲醛制备二碘化二环氧二苯并二苯并[ c，k ] [1,9]二恶环环十六烷的简便策略被提出。亲电子大环化可以在温和的条件下进行，并且以克为单位。此外，所得碘化物的钯催化的偶联和还原反应可以有效地提供氧杂大环。

更新日期：2017-09-08

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