Noriaki Yamauchi

Diacetone glucose architecture as a chirality template. II.1 Versatile synthon for the chiral deuterium labeling and synthesis of all diastereoisomers of chirally monodeuterated glycerol

Abstract Chirally deuterated ethylene oxide derivatives attached to a diacetone glucose template were developed as new versatile synthons for chiral deuterium labeling. All four diastereoisomers of chirally monodeuterated glycerol were also synthesized by chirality transcription from the same template.

Mechanistic and stereochemical studies on Ferrier reaction by means of chirally deuterated glucose

Abstract The mechanism of Ferrier reaction, cyclitol formation from 5-enopyranosides, was investigated by using (E)-selectively deuterated methyl [6- 2 H]-2,3,4-tri-O-benzyl-α- D -xylo-hex-5-enopyranoside. The overall reaction was non-stereoselective with respect to the C-6 position of the substrate. Crucial organomercurial intermediates were isolated and characterized. The loss of stereochemical integrity was attributed mainly to the formation of an open-chain organomercurial and its rapid equilibrium. A mechanism involving radical intermediate is suggested.

Structural Diversity of the Membrane Core Lipids of Extreme Halophiles.

The structural diversity of the core lipids of extreme halophiles Haloarcula japonica and Halobacterium halobium was investigated. The most significant difference is that Ha. japonica contains sn-2,3-di-O-phytanylglycerol exclusively as the core lipid, whereas Hb. halobium contains both sn-2,3-di-O-phytanylglycerol and sn-2-O-sesterterpanyl (3,7,11,15,19-pentamethyleicosanyl)-3-O-phytanylglycerol.

Diacetone-glucose architecture as a chirality template. Part9.1 Enantioselective synthesis of(R)-mevalonolactone and(R)-[2H9]mevalonolactone oncarbohydrate template

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.