An efficient and flexible route to (+)-polyoxamic acid using diastereoselective epoxidation of 1-arylthio-1-nitroalkenes
Abstract
Polyoxamic acid 4a is prepared by a short and efficient process in which the key steps are the highly diastereoselective nucleophilic epoxidation of the D-threitol-derived alkene 6 using potassium tert-butylperoxide, followed by reaction of the oxirane 7a with ammonia.