Metal-catalyzed cyclopropanation on the 8-oxabicyclo[3.2.1]oct-6-ene template

Cyclopropanations of an 8-oxabicyclo[3.2.1]octene substrate using diazocarbonyl compounds provided exo, exo-cyclopropanated products as the sole or major diastereomeric oxatricyclic products. Reductive cleavage of a meso-oxatricyclic ketone by samarium iodide resulted in desymmetrization without concomitant oxygen bridge cleavage.