Asymmetric total synthesis of 5′-epi-cochliomycin C

Asymmetric total synthesis of one of the stereoisomers of naturally occurring chlorine containing 14-membered ring macrolide cochliomycin-F (5′-epi) has been described in this article. The main highlight of the presented synthetic strategy involves a highly regioselective chlorination and Julia–Kocienski olefination with a highly substituted aromatic chloro-aldehyde to create the required E-olefinic unsaturation in the target molecule. Mitsunobu macrolactonization reaction at the late stage enables us to synthesize the target molecule.