Synthesis of Methylene Tetrahydrofurane-Fused Carbohydrates |
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| Authors: | Maryam Ahmadian-Moghaddam Niels R M Reintjens Dr Martin D Witte Dr Adriaan J Minnaard |
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| Institution: | Stratingh Institute of Chemistry, University of Groningen, Nijenborgh 7, 9747 AG Groningen, Netherlands |
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| Abstract: | A reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether functionality serves as a handle that enables modification in biological systems via photoclick chemistry. The approach is based on the regioselective oxidation of the C-3 hydroxy group in gluco-configured pyranosides, followed by stereoselective indium-mediated allylation. The ring formation is induced by an iodocyclization reaction with a neighboring hydroxy group. Subsequent dehydrohalogenation affords the desired methylene-tetrahydrofuran-containing carbohydrates. |
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| Keywords: | carbohydrates enol ether iodocyclization photoclick site selectivity |
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