Highly regio- and stereospecific hydroxylation of C-1 position of 2-deacetoxytaxinine J derivative with DMDO

A simple chemical oxidation of 2-deacetoxytaxinine J derivative 3 using an excess of dimethyldioxirane (DMDO) results in a highly regio- and stereospecific hydroxylation of the C-1 position to afford the 1β-hydroxy α-4(20)-epoxide 6 and 1β-hydroxy β-4(20)-epoxide 7. A plausible mechanism of this reaction via ‘insertion’ is proposed.