Total Synthesis of Neooxazolomycin

Abstract

Two sides to the story: Neooxazolomycin, a member of the oxazolomycin family of antibiotics, was synthesized in naturally occurring form by a convergent approach. This highly stereoselective strategy consists of a Tamao hydrosilylation, palladium-catalyzed enolate alkenylation, dihydroxylation accompanied by lactonization, and a Nozaki–Hiyama–Kishi reaction to construct the right-hand segment as well as an improved route to the left-hand segment.