Stereocontrolled oxygenation of camphor derivatives as an prelude to the complete beta-ring functionalization of potential precursors to taxol and structural analogs thereof

Experimental studies indicate that both dimethyl dioxirane and Davis oxaziridine reagent are capable of alpha-oxygenating camphor-derived unsaturated ketones. Reaction of the MOM derivatives of these ketones with cyclohexenyllithium reagents, followed by anion oxy-Cope rearrangement produces tricyclic products. The C-2, C-9, C-10 B-ring oxygenation pattern of these derivatives is similar to that in taxol.