Synthesis of 4-aminotetrahydropyran scaffolds for drug discovery

Publication date: Available online 22 February 2017
Source:Bioorganic & Medicinal Chemistry
Author(s): 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.

Graphical abstract

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