Complete construction: The total synthesis of IKD-8344, a novel 28-membered ring macrodiolide antibiotic (see structure), was accomplished by employing Williamson ether synthesis, β-alkoxymethacrylate radical cyclization, and Yamaguchi lactonization reactions. This synthesis is another example of the application of β-alkoxymethacrylate radical cyclization reactions for the stereoselective construction of complex oxacyclic natural products.