[3+2] Cycloaddition reactions: a simple entry to the 1-aza-2-oxo-3,4,5,6-tetrahydroxybicyclo[3.3.0]octane ring system |
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Authors: | Ashim Roy |
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Affiliation: | Division of Medicinal Chemistry, Indian Institute of Chemical Biology, Jadavpur, Kolkata 700032, India |
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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. |
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Keywords: | Nitrone cycloaddition reaction Synthesis Bicyclic lactams Azabicyclo[3.3.0]octane smallcaps" >d-glucose |
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