Herein we describe a versatile approach to the pyrrolizidine alkaloids skeleton by tailoring our original strategy already used for the pyrrolidine iminosugars synthesis. The key steps are the regio- and stereoselective azidolysis of the suitable chiral vinyl epoxide and then asymmetric dihydmxylation of the corresponding azido alcohol by using (DHQ)(2)AQN as the ligand. Further optimized elaborations addressed to the closure of the two rings allowed us to achieve the target iminosugar with complete stereocontml. The wide range of pyrmlizidine iminosugars' biological properties make them a key focus of new drug research and therefore the development of synthetic strategies for obtaining them is of decisive importance.