Exploitation of Intramolecular Glaser–Eglinton–Hay Macrocyclization for the Synthesis of New Classes of Optically Active Aza-Oxo-Thia Polyether Macrocycles from Amino Alcohol Building Blocks

Abstract

We report an intramolecular Glaser–Eglinton–Hay coupling as an unprecedented route for assembling optically active aza-oxo polyether macrocycles containing a 1,3-diyne unit from enantiopure amino alcohol building blocks and suitable linkers. Furthermore, the conversion of the 1,3-diyne unit of the aza-oxo polyether macrocycles into a thiophene ring led to the assembly of new classes of optically active aza-oxa-thia (heterotopic) polyether macrocycle analogues of classical 18-C-6 and 18-C-5 systems.