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Stereocontrolled synthesis of 2,4-diamino-3-hydroxyacids starting from diketopiperazines: A new route for the preparation of statine analogues
Journal article   Peer reviewed

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

Daniel Farran, L. Toupet, Jean Martinez and Georges Dewynter
Organic Letters, Vol.9(23), pp.4833-4836
2007

Abstract

stereoselective-synthesis 4-amino-3-hydroxy-5-phenylpentanoic acid stereospecific synthesis aspartic proteinases hiv-1 proteinase renin inhibitors n-protected statine tetramic acids pepstatin amino-acid
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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