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