This study was designed to create a series of spirolactone compounds produced through an oxidative spiroannulation reaction, each with a different substituent at the benzylic position. The effect, if any, on the diastereoselectivity of the spiroannulation reaction caused by the benzylic substitution would then be determined by ¹H-NMR. Several synthetic methodologies were employed in attempts to produce these compounds but only a single compound was successfully produced in 27% yield in 5 steps. This compound had a hydroxyl function at the benzylic position and showed total enantioselectivity in the spiroannulation reaction. Several unique properties of the intermediate molecules created in these studies were discovered while attempting to synthesize the target molecules. --P. iii.
