Stereoselective Total Synthesis of Achaetolide from L-Malic Acid

A convergent total synthesis of achaetolide is described. The key steps include a Horner-Wadsworth-Emmons olefination, CBS reduction to install the stereochemistry at the C9 center, stereoselective vinylation to introduce the chiral center at C6, and finally a ring-closing metathesis (RCM) reaction to construct the ten-membered lactone of the molecule.