First total synthesis of theopederin B

Total synthesis of theopederin B, isolated from marine sponge, was accomplished by coupling pederic acid, as the left half, with trioxodecaline amine as the right half. Key reactions for synthesizing the amine were SmI2-promoted Reformatsky reaction, stereoselective allylation followed by Sharpless asymmetric epoxidation for construction of the functionalized side chain, and 1,3-dioxane ring construction followed by azide insertion.