Bicyclic lactams as templates for peptidomimetics. Studies on stereoselective synthetic routes to 6-oxoperhydropyrrolo[1,2-α]pyrazines

Article abstract of DOI:10.1016/0040-4020(96)00842-3

The synthesis of 4,7,7-trisubstituted 6-oxoperhydropyrrolo[1,2-α]pyrazines, as spacer templates for peptidomimetics, from the corresponding 3,6-dioxo analogues is described using different reduction methods. An alternative approach, based on the intramolecular reductive amination of 4-ketodiesters derived from Ψ[CH₂NH] pseudodipeptides and subsequent γ-lactamization, was also used for the stereoselective preparation of these templates.