5H-6-oxo-2,3,4,4a,7,7a-hexahydropyrano[2,3-b]pyrrole and the preparation thereof

摘要

Conformationally restricted peptide analogs incorporating a rigid beta -bend are formed by replacing a portion of the peptide backbone chain with a bicyclic heterocycle, 5H-6-oxo-2,3,4,4a,7,7a-hexahydropyrano[2,3-b]pyrrole. Properly substituted derivatives of the pyranopyrrole are conformationally rigid and cannot assume non- beta -bend conformations in the interior of the peptide chain, while the terminal binding residues are maintained in the proper orientation for receptor interaction. Also described are a novel intermediate for preparation of the peptide analogs and a method for preparation of the intermediate.