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[3+2] Cycloaddition reactions: a simple entry to the 1-aza-2-oxo-3,4,5,6-tetrahydroxybicyclo[3.3.0]octane ring system
Authors:Ashim Roy
Affiliation:Division of Medicinal Chemistry, Indian Institute of Chemical Biology, Jadavpur, Kolkata 700032, India
Abstract:The [3+2] intramolecular nitrone cycloaddition (INC) reaction on appropriately designed olefinic nitrones derived from d-glucose, having the nitrone at C-1 and α,β-unsaturated ester functionalities at C-5 of the sugar backbone, afforded the isoxazolidine fused carbocycles 11-13, which were subsequently transformed into the chiral, tetrahydroxylated cis-azabicyclo[3.3.0]octanones 14-18 in good yields.
Keywords:Nitrone cycloaddition reaction   Synthesis   Bicyclic lactams   Azabicyclo[3.3.0]octane     smallcaps"  >d-glucose
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