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Extension of the Modified Julia Olefination on Carboxylic Acid Derivatives: Scope and Applications
Synlett ( IF 1.7 ) Pub Date : 2017-10-16 , DOI: 10.1055/s-0036-1590916
David Gueyrard

This account relates our work in the field of modified Julia olefination to extend this very useful olefination method to carboxylic acid derivatives. Since our preliminary results on lactones in 2005, the reaction has been extended to a large range of derivatives (lactams, imides and anhydrides) through an intra- or intermolecular process leading to a great variety of structures (enol ethers, enamides and exo enol esters). This article will also focus on the application of this methodology for the preparation of biologically interesting compounds and/or total syntheses of natural products such as C-disaccharide, bistramide A, jaspine B and maculalactone B. 1 Introduction 2 Modified Julia Olefination on Lactones 2.1 Methylene Enol Ether Synthesis 2.2 Substituted Enol Ether Synthesis 2.3 Monofluorinated Enol Ether Synthesis 2.4 Difluorinated Enol Ether Synthesis 3 Applications 3.1 Spiroketal Synthesis 3.2 Spirocompound Synthesis 3.3 Pseudodisaccharide Synthesis 3.4 Total Synthesis of Jaspine B 4 Modified Julia Olefination on Other Carboxylic Acid Derivatives 4.1 Lactam Olefination and Spiroaminal Synthesis 4.2 Bicyclic Enamide Synthesis by Intramolecular Modified Julia Olefination on Imides 4.3 Modified Julia Olefination on Anhydrides 5 Conclusion

中文翻译:

羧酸衍生物上改性 Julia 烯烃的扩展:范围和应用

这个帐户将我们在改性 Julia 烯化领域的工作联系起来,以将这种非常有用的烯化方法扩展到羧酸衍生物。自从我们在 2005 年对内酯进行初步研究以来,该反应已通过分子内或分子间过程扩展到多种衍生物(内酰胺、酰亚胺和酸酐),从而产生多种结构(烯醇醚、烯酰胺和外烯醇酯) )。本文还将重点介绍该方法在制备具有生物学意义的化合物和/或天然产物(如 C-二糖、双链酰胺 A、茉莉花 B 和黄斑内酯 B)的全合成中的应用。 1 介绍 2 内酯 2.1 上的改性 Julia Olefination亚甲基烯醇醚合成 2.2 取代烯醇醚合成 2.3 单氟化烯醇醚合成 2.
更新日期:2017-10-16
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