Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside

Tetrahedron Lett. 2010 Jul 1;51(29):3789-3791. doi: 10.1016/j.tetlet.2010.05.062.

Abstract

Treatment of nitroso Diels-Alder cycloadducts 1 with diazomethane in the presence of palladium acetate gives synthetically useful exo-6-oxa-7-azatricyclo[3.2.1.02,4]octane derivatives 7 in good to excellent yield. Using this methodology, a conformationally restricted 2',3'-methano carbocyclic nucleoside was efficiently synthesized from nitroso cycloadduct 1a in 7 steps.