Extension of the Modified Julia Olefination on Carboxylic Acid Derivatives: Scope and Applications

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. 1Introduction 2Modified Julia Olefination on Lactones 2.1Methylene Enol Ether Synthesis 2.2Substituted Enol Ether Synthesis 2.3Monofluorinated Enol Ether Synthesis 2.4Difluorinated Enol Ether Synthesis 3Applications 3.1Spiroketal Synthesis 3.2Spirocompound Synthesis 3.3Pseudodisaccharide Synthesis 3.4Total Synthesis of Jaspine B 4Modified Julia Olefination on Other Carboxylic Acid Derivatives 4.1Lactam Olefination and Spiroaminal Synthesis 4.2Bicyclic Enamide Synthesis by Intramolecular Modified Julia Olefination on Imides 4.3Modified Julia Olefination on Anhydrides 5Conclusion