Julia–Kocienski olefination: a key reaction for the synthesis of macrolides

The unification of carbonyl compounds and heteroaryl sulfones provides one of the best methods for the construction of C–C double bond for synthetic chemists in designing synthetic routes to natural and non-natural products. For the C–C double bond formation, olefination, particularly the Julia–Kocienski olefination (JK-olefination) has emerged as a powerful key reaction in the synthesis of natural products that contain macrocycles. Molecules of interest include macrolides, whose biological importance, lack of natural resources, and interesting structure placed a challenge among the scientific community for their total synthesis. Thus, for systematic documentation we have summarized the synthetic approaches toward several important macrolides highlighting the Julia–Kocienski olefination as one of the key steps. This review is intended to show the utility of the Julia–Kocienski olefination in the synthesis of biologically important macrocyclic natural products.

Graphical abstractThis review is an overview of the Julia–Kocienski olefination for the formation of stereoselective C–C double bond in the synthesis of biologically active natural products, analogues, and building blocks containing macrocycles, in particular, macrolides.Figure optionsDownload full-size imageDownload as PowerPoint slide