Peer-Reviewed Journal Details
Mandatory Fields
O'Reilly, C,O'Brien, C,Murphy, PV
2009
August
Tetrahedron Letters
Synthesis of a constrained polyfunctional bicyclic iminocyclitol scaffold from L-sorbose via a tandem sequence including stereoselective intramolecular Huisgen cycloaddition
Published
()
Optional Fields
RING-CLOSING METATHESIS 1,3-DIPOLAR CYCLOADDITION GLYCOSIDASE INHIBITORS MEDICINAL CHEMISTRY BIOLOGICAL-ACTIVITY 1-DEOXYNOJIRIMYCIN DERIVATIVES MIMETICS PEPTIDOMIMETICS IMINOSUGARS
50
4427
4429
The synthesis of a functionalized (azido, amino, and hydroxy) 8-oxa-3-azabicyclo[3.2.1]octane framework and its conversion into a protected sugar amino acid and a tricyclic framework is described. The sequence includes a one-pot Huisgen 1,3-dipolar cycloaddition, with decomposition to an aziridine and subsequent ring opening by azide. The stereoselectivity observed in the Huisgen cycloaddition reaction is attributed to minimization of allylic strain. (C) 2009 Elsevier Ltd. All rights reserved.
DOI 10.1016/j.tetlet.2009.05.060
Grant Details
Publication Themes