13-Step total synthesis of Dendrodolide K following iterative Bartlett–Smith iodocarbonate cyclization

Abstract

A convergent total synthesis of Dendrodolide K has been achieved starting from commercially available homoallyl alcohol 17 in 13 longest linear sequence with 18.2% overall yield. The key features of this synthesis are Bartlett–Smith iodocarbonate cyclization reaction for the construction of 1,3-syn centers of the polyol system, Sharpless epoxidation followed by titanocene induced deoxygenation of 2,3-epoxy alcohol to fix stereogenic center at C-3 position, Yamaguchi esterification followed by ring-closing metathesis (RCM) reaction to form the macrolactone.