Issue 5, 2015

New building blocks for iminosugars: a concise synthesis of polyhydroxylated N-alkoxypiperidines through an intramolecular azepine ring contraction

Abstract

Polyhydroxylated piperidines are a functionally rich class of biologically active molecules that have broad therapeutic potential. Recently developed aza-[4 + 3] cycloadditions of putative aza-oxyallylic cations provide heterocyclic scaffolds that enabled a concise synthesis of polyhydoxylated piperidines. Chemoselective amide reduction and reductive hemiaminal ring opening was achieved in one pot by the action of aluminium hydride generated in situ via aluminium chloride and lithium aluminium hydride. Aziridinium ion mediated ring contraction and chloride displacement was triggered by silver acetate, followed by simple acetate hydrolysis using potassium carbonate to give four tetrahydropyridine diols. Olefin oxidation by osmium tetroxide installed the final hydroxyl groups, which yielded four novel polyhydroxylated N-alkoxypiperidines in good overall yield and high diastereoselectivity.

Graphical abstract: New building blocks for iminosugars: a concise synthesis of polyhydroxylated N-alkoxypiperidines through an intramolecular azepine ring contraction

Supplementary files

Article information

Article type
Research Article
Submitted
16 12 2014
Accepted
12 3 2015
First published
13 3 2015

Org. Chem. Front., 2015,2, 497-501

Author version available

New building blocks for iminosugars: a concise synthesis of polyhydroxylated N-alkoxypiperidines through an intramolecular azepine ring contraction

K. L. Barnes, K. Chen, V. J. Catalano and C. S. Jeffrey, Org. Chem. Front., 2015, 2, 497 DOI: 10.1039/C4QO00330F

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