DIACETONE-GLUCOSE ARCHITECTURE AS A CHIRALITY TEMPLATE .9. ENANTIOSELECTIVE SYNTHESIS OF (R)-MEVALONOLACTONE AND (R)-[H-2(9)]MEVALONOLACTONE ON CARBOHYDRATE TEMPLATE

A highly enantioselective synthetic methodology for (R)-mevalonolacton e has been developed based upon the chirality-transcription approach u sing a chiral template, diacetone-D-glucos-3-ulose 2. (R)-Mevalonolact one 1a is prepared from ketone 2 in 5 steps in 11% overall yield, This methodology is further applied to the synthesis of fully deuteriated (R)-[H-2(9)]mevalonolactone 1b starting from ketone 2 and methyl [H-2( 7)]senecioate 7.