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. (C) 2013 Elsevier Ltd. All rights reserved.