Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.
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.
Ji
Cheng
C
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana, 46556, United States.
Miller
Marvin J
MJ