Synthesis of 4-aminotetrahydropyran scaffolds for drug discovery. Issue 7 (1st April 2017)

• Record Type: Journal Article
• Authors: Nortcliffe, Andrew; Milne, Gavin D.S.; Hamza, Daniel; Moody, Christopher J.
• Is Part Of: Bioorganic & medicinal chemistry. Volume 25:Issue 7(2017)
• Page Start: 2218
• Page End: 2225
• Publication Date: 2017-04-01
• Subjects: Tetrahydropyran -- Prins cyclisation -- Amine functionalisation -- Azide-alkyne cycloaddition; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2017.02.039
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: 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 sp 3 -rich scaffolds useful for drug discovery.