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

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Masashi Kishida, Noriaki Yamauchi, Keiju Sawada, Yuji Ohashi, Tadashi Eguchi and Katsumi Kakinuma


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.


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