Applications of thiyl radical cyclizations for the synthesis of thiosugars.

School of Chemistry, Trinity College Dublin, Trinity Biomedical Sciences Insitute, 152-160 Pearse Street, Dublin 2, Ireland.

Organic letters 2013 Feb 1

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The use of intramolecular thiyl radical cyclizations for the synthesis of thiosugars has been investigated, and a new free-radical-based methodology for the synthesis of biologically important thiosugars has been developed. The methodology is mild and proceeds via either 6-endo or 5-exo cyclization to furnish the thiosugar ring. This represents the first examples of thiyl radical cyclization being applied to the synthesis of thiosugars.