Synthesis of 4′-thionucleosides by 1,3-dipolar cycloadditions of the simplest thiocarbonyl ylide with alkenes bearing electron-withdrawing groups |
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Authors: | Antonino Corsaro Venerando Pistarà Elisa Vittorino |
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Institution: | a Dipartimento di Scienze Chimiche, Università di Catania, viale A. Doria 6, Catania 95125, Italy b Dipartimento Farmaco-Chimico, Università di Messina, via SS. Annunziata, Messina 98168, Italy |
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Abstract: | Reactions of the simplest thiocarbonyl ylide with a variety of appropriate alkenes bearing electron-withdrawing substituents afforded the corresponding tetrahydrothiophenes, which could be easily elaborated into hydroxy and hydroxymethyl derivatives and then coupled with nucleobases to produce different 4′-thionucleosides. Particularly, α- and β-anomers of 1-3,4-bis(hydroxymethyl)tetrahydro-2-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with dimethyl fumarate and maleate, while 1-4-(hydroxymethyl)tetrahydro-2-thienyl]- and 1-4-(hydroxymethyl)tetrahydro-3-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with a chiral α,β-unsaturated amide. These processes, simple in the experimental conditions and large availability of the starting materials, affording moderate to good yields of 4′-thionucleosides, represent an optimum alternative to those, already known, based on sugars, which often have the drawbacks of a higher number of steps and lower yields. |
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Keywords: | Thionucleosides 1 3-Dipolar cycloaddition Thiocarbonyl ylide Antiviral |
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