The first example of a highly stereoselective intramolecular radical cyclisation of a cyclopentenol derivative

Article abstract of DOI:10.1016/S0040-4039(97)00211-6

Silyl methylene radical cyclisation of a β-allylic cyclopentaannulated derivative of glucose leads to a single cis fused tricyclic ring system whereas the same cyclisation of the corresponding a derivative leads to a mixture of cis and trans fused products. These results can be explained by the preference for the formation of the cis fused 5,6-ring system even when this does not involve reaction from the least hindered side of the molecule.