Synthetic study of polyoxypeptin: stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline

The first synthesis of (2S,3R)-3-hydroxy-3-methylproline, which is a novel amino acid of polyoxypeptin, a potent inducer of apoptosis in human pancreatic carcinoma AsPC-1, was accomplished. The key feature of the synthesis is the palladium-catalyzed intramolecular N-allylation of alkenyloxirane to the pyrrolidine ring.