Intramolecular nitrone cycloaddition reaction on carbohydrate-based precursors: application in the synthesis of spironucleosides and spirobisnucleosides |
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Authors: | Singha Kaushik Roy Atanu Dutta Pradeep K Tripathi Subhankar Sahabuddin Sk Achari Basudeb Mandal Sukhendu B |
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Institution: | Division of Medicinal Chemistry, Indian Institute of Chemical Biology, Jadavpur, Kolkata 700 032, India. |
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Abstract: | A simple synthesis of chiral spironucleosides and spirobisnucleosides is described. Intramolecular 1,3-dipolar nitrone cycloaddition reaction of d-glucose-derived precursors having olefin at C-3 and nitrone at C-5, C-1, or C-2 (in nor-series) furnished bisisoxazolidinospirocycles 4-7, 11, and 12 in good yields. Reductive ring opening of the isoxazolidine moieties in 4-6 followed by construction of a nucleoside base upon the generated amino groups smoothly yielded spirobisnucleosides 17 and 18 and spironucleosides 20 and 21. |
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