Pascale Hoffmann

Stereoselective C-C bond formation in carbohydrates by radical cyclization reactions-II

Abstract The synthesis of the bicyclic acetals 8 from the glycal 1 using a radical cyclization reaction is described.

Stereoselective CC bond formation in carbohydrates by radical cyclization reactions-III. Strategy for the preparation of C(1)-glycosides

Abstract A new strategy for the stereoselective synthesis of α- and β-C(1)-glycosides based on an intramolecular radical cyclization reaction is described. Intramolecular hydrogen atom transfer was observed depending on the concentration of the reagents, the conformation and the substitution of the cyclized radical.

Stereoselective CC bond formation in carbohydrates by radical cyclization reactions-I.

Abstract A three steps synthesis of α-zC(2) branched pyranosides from the glycal 1 is described.

Stereocontrol in radical cyclizations on sugar templates

Abstract The radical cyclization of alkyl hex-2-enopyranosides provides a stereocontrolled route to fused furanopyranes. The intermediate radical is generated either via the reduction of the appropriate halide by tin hydride or via sulfonyl radical addition to allyl hex-2-enopyranosides. The two methodologies are compared with respect to diastereoselectivity. Stereocontrol is discussed on the basis of conformational preference in the transition state.

Stereoselective CC bond formation in carbohydrates by radical cyclization reactions-IV. Application for the synthesis of α-C(1)-glucosides

Abstract The synthesis of α-C(1)-glucosides is reported using our new strategy for the C C bond formation at the anomeric center by radical cyclization reactions.

A new protected form of glucuronic acid for the synthesis of labile 1-O-acyl-β-D-glucuronides

Abstract A new approach to functionalized 1-O-acyl-β-D-glucuronides is described. An essential element of this strategy is the use of the easily removable allyloxycarbonyl group for the protection of the hydroxylic functions of glucuronic acid.