Samarium diiodide-induced radical cyclization of oxime ether connected with formyl group: Synthesis of 4-pyrimidinyl- and 4-purinylpyrrolidin-3-ol nucleoside analogues

Article abstract of DOI:10.1016/S0040-4020(98)00274-9

SmI₂-induced 5-exo-trig radical cyclization of oxime ether intramolecularly connected with the formyl group was found to be particularly effective for preparing cyclic trans-amino alcohol in good chemical yield with a high degree of stereoselectivity. Its successful application to the synthesis of a novel class of 4-pyrimidinyl- and 4-purinylpyrrolidin-3-ol nucleoside analogues is also described.