Synthesis of rumphellaone A via epoxy nitrile cyclization

The first enantioselective total synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane isolated from the gorgonian coral Rumphella antipathies, has been achieved from a known olefinic alcohol by a 16-step sequence involving Storkʹs epoxy nitrile cyclization as the key step to concomitantly install a cyclobutane ring and three contiguous stereogenic centers contained in the molecule.