Fragments of 2-aminoetanol and 2-amino-1,3-diol are present in many natural compounds. Both the amino group and the hydroxyls are frequently found in stereogenic centers with a defined configuration, which is essential for the biological activity of the compound. Consequently, we can find this fragment in aza-sugars like the Desoxymannojirmycin (1), amino-sugars like the Daunsamine (2), aminocyclitols like the 2-Desoxiestreptamine (3), amino acids like (2R, 3R)-2-amino-3-hydroxy-3-cyclohexylpropanoic acid (4) or sphingolipids like the sphingadienine (5).

Our research group is working in the enantioselective synthesis of these families of compounds, developing convergent approximations, based in the regioselective opening of epoxides or sulphates prepared by Sharpless asymmetric epoxidation or dihydroxylations. The nucleophiles used in these reactions are several kinds of amines and synthetic equivalents of ammonia. The key factor of our approximation is to control the regioselectivity of the ring opening process, because it allows us to obtain both centers with completely determined anti configuration. Besides, the versatility of both Sharpless epoxidation and dihydroxilation in the selection of the product configuration, simply by changing the ligand, has allowed us to get access to a big number of amino alcohols with the desired stereochemistry.

The ring-closing metathesis reaction (RCM) is one of the most powerful tools for the preparation of cyclic compounds. Taking advantage of the alkene fragment present in unsaturated epoxides, several synthetic methodologies for the preparation of bioactive compounds have been developed. For example, the ring-opening in C-3 of the 2,3-epoxy-hex-5-en-1-ol with nitrogen nucleophiles, combined with an RCM reaction as a key step, has allowed the preparation of several aminocyclitols and hydroxypipecolic acids. The same unsaturated aminidol has been the starting material for our stereodivergent approximation to the synthesis of 3-amino-2,3,6-desoxysugars. Some of these compounds are compounds of antracyclinic antibiotics with antitumoral activity.

A part from this, the epoxide ring-opening in C2 with a synthetic equivalent of the allylamine on the 2,3-epoxypent-4-en-1-ol, combined with a reaction of RCM has allowed the development of a general synthesis of aza-sugars with activity as glycosidase inhibitors. The ring-opening in C3 with allylamine has lead to polyhydropyrrolidines.