Synthesis of 4-aminotetrahydropyran scaffolds for drug discovery
Andrew Nortcliffe, Gavin D.S. Milne, Daniel Hamza, Christopher J. Moody
Functionalised tetrahydropyran scaffolds were prepared using a tethered enol-ether Prins cyclisation and elaborated to show their potential use in library synthesis. The key 4-hydroxytetrahydropyran scaffold could be readily manipulated to the 4-azidotetrahydropyran that could be elaborated via copper catalysed azide-alkyne cycloaddition or by reduction to the amine, to provide sp3-rich scaffolds useful for drug discovery.
Ref: Bioorganic & Medicinal Chemistry (2017), 25(7), 2218-2225.