Stereocontrolled synthesis of 2,4-diamino-3-hydroxyacids starting from diketopiperazines: a new route for the preparation of statine analogues |
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Authors: | Farran Daniel Toupet Loïc Martinez Jean Dewynter Georges |
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Institution: | Institut des Biomolécules Max Mousseron, UMR 5247, Université Montpellier 2, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France. |
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Abstract: | 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. |
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