Ana Pedregosa

Stereoselective synthesis of substituted exo-glycals from 1-exo-methylene pyranoses

Halo-exo-glycals of the gluco-, manno- and galacto- series, readily prepared by reaction of 1-exo-methylene pyranoses with iodonium dicollidinium triflate (IDCT), undergo Suzuki or B-alkyl Suzuki cross-coupling reactions with boronic acids or alkyl boranes to yield, in a stereoselective manner, functionalized exo-glycals.

One-pot synthesis of 1-exo-alkylidene-2,3-anhydro furanoses: convenient precursors for exo-glycals and functionalized C-glycals

1-exo-Methylene-2,3-anhydro furanoses, obtained from C-glycals in a one-pot, three step operation can be readily transformed into functionalized C-glycals by palladium-catalyzed nucleophilic addition.

A general method for convergent synthesis of functionalized exo-glycals based on halogenation and Suzuki cross-coupling of 1-exo-methylene sugars.

Functionalized exo-glycals can be readily obtained by palladium catalyzed Suzuki cross-coupling of halo-exo-glycals with boronic acids.

Three-Component Assembly of Amines, Boronic Acids, and a Polyfunctionalized Furanose: A Concise Entry to Furanose-Based Carbohydrate Templates

A highly functionalyzed furanose derivative, accessible in five steps from D-mannose, comprising a halo-alkenyl allylic-oxirane system, undergoes a palladium catalyzed one-pot, three component, assembly with boronic acids (or alkyl boranes) and amines to give, in a complete regio- and stereocontrolled manner, a sugar based derivative with two sites of molecular diversity.