Alejandro Cordero-Vargas

Synthesis of substituted naphthalenes from α-tetralones generated by a xanthate radical addition–cyclisation sequence

A simple, highly efficient and cheap synthesis of substituted naphthalenes is reported. These aromatic compounds can be easily prepared in acidic or basic conditions from [small alpha]-tetralones, obtained by a xanthate-mediated addition-cyclisation sequence.

Stereoselective C-glycosidation of D-fucose derivatives directed by the protective groups.

Stereoselectivity in the C-glycosidation of lactones derived from D-fucose by following Kishis method, which involves the addition of a nucleophile onto a carbohydrate-derived lactone and subsequent reduction of the lactol, was found to be reliant on the nature of the C2 and C3 protective groups. Lactones bearing TBDMS protecting groups selectively afford 1,3-trans products (α anomer), in which the stereoselective outcome is in apparent concordance with Woerpels model. On the other hand, their benzylated congeners produce the 1,3-cis products (β anomer) as the major diastereoisomers. The latter results suggest an abnormal behavior during the stereoselective nucleophilic substitution at the anomeric position of the benzylated lactones.