Efficient Synthesis of Structurally Diverse Diazabicycloalkanes: Scaffolds for Modular Dipeptide Mimetics with Tunable Backbone Conformations

摘要: A stereoselective synthesis of new dipeptide mimetics based on a diazabicycloalkane scaffold is reported. The route starts from enantiomerically pure azabicycloalkenes 1 that are bis(hydroxylated) and coupled N-terminally to second amino acid. key step the reaction sequence an oxidative cleavage resulting dipeptides 5 give highly functionalised diazabicycloalkanes 6, which can be easily converted into number with defined variable stereochemistry different acid side chains. backbone dihedral angles within these tuned by varying ring sizes scaffold. syntheses conformationally constrained analogues in four five steps presented. With 19a−c, suitable linker moieties for conjugation other functional molecules like markers or solid phases introduced, making compounds modular might find applications as ligands solid-phase-attached scaffolds combinatorial chemistry. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)