Diacetone-glucose architecture as a chirality template. Part 9.1 Enantioselective synthesis of (R)-mevalonolactone and (R)-[2H9]mevalonolactone on carbohydrate template

Abstract

A highly enantioselective synthetic methodology for (R)-mevalonolactone has been developed based upon the chirality-transcription approach using a chiral template, diacetone-D-glucos-3-ulose 2. (R)-Mevalonolactone 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)-[²H₉]mevalonolactone 1b starting from ketone 2 and methyl [²H₇]senecioate 7.