Stereocontrolled synthesis of 2,4-diamino-3-hydroxyacids starting from diketopiperazines: a new route for the preparation of statine analogues.

Chiral 3-aminopyrrolidine-2,4-diones, obtained by transannular rearrangement of activated diketopiperazines, could be a springboard toward an exceptional stereoselective synthesis of original 2-disubstituted statines. After a selective reduction of the pyrrolidine-2,4-diones, the access to opened 2,4-diamino-3-hydroxyacid esters was carried out by a subsequent alkaline treatment or directly through a tandem reduction-solvolysis.