Total stereocontrolled synthesis of a novel pyrrolizidine iminosugar

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 dihydroxylation of the corresponding azido alcohol by using (DHQ)2AQN as the ligand. Further optimized elaborations addressed to the closure of the two rings allowed us to achieve the target iminosugar with complete stereocontrol. The wide range of pyrrolizidine 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. [Display omitted] •A versatile approach to the pyrrolizidine alkaloids skeleton is described.•The key steps are the selective azidolysis of a chiral vinyl epoxide and then asymmetric dihydroxylation of the corresponding azido alcohol.•Using (DHQ)2AQN as ligand, the enantioselective synthesis of a novel pyrrolizidine iminosugar was developed.