Discodermolide was discovered in 1990 and with its discovery set off an expansive medicinal chemistry program fueled by many groups’ research. It acts as a microtubule stabilizer, which makes it a potential anti-cancer agent. The synthesis of simplified discodermolide analogs is reported here. These analogs use simplified versions of the lactone and carbamate fragments, which are then coupled via olefin metathesis. Hologram quantitative structure-activity relationship (HQSAR) is also used to show that an olefin linker inserted by olefin metathesis as viable simple alternatives to the complex middle portion usually found in the parent molecule.