Synthesis of 2(R),3-dihydroxypropyl and 2(R),3(R)-dihydroxybutyl beta-D-fructopyranosides and some derivatives.

The synthesis of 2(R),3-dihydroxypropyl and 2(R),3(R)-dihydroxybutyl beta-d-fructopyranosides, and some derivatives, employing Sharpless-type catalytic asymmetric dihydroxylation procedures is described. Some aspects of the reactions, including stereoselectivities and chemical evidence for the assigned stereochemistry of the main products are reported.

alpha-Cycloalkyl-substituted omega-keto-dicarboxylic acids as lipid regulating agents.

A series of cycloalkyl-substituted oxo-alkanedicarboxylic acids have been prepared by the TosMIC methodology departing from haloalkyl-substituted cycloalkylcarboxylic esters. cyclopropyl derivatives showed IC(50) activity in the 0.3-1.

Synthesis of 1-deoxy-L-gulonojirimycin (L-guloDNJ) and 1-deoxy-D-talonojirimycin (D-taloDNJ).

Carbohydrate based syntheses of azasugars with unusual configurations viz. 1,5-dideoxy-1,5-imino-L-gulitol (L-guloDNJ) and 1,5-dideoxy-1,5-imino-L-talitol (L-taloDNJ) are reported, from D-mannose and D-fructose, respectively. The key steps in both syntheses involved reductive aminative cyclizations.