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.
Farran
Daniel
D
Institut des Biomolécules Max Mousseron, UMR 5247, Université Montpellier 2, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.
Toupet
Loïc
L
Martinez
Jean
J
Dewynter
Georges
G
D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D054659:Diketopiperazines / Q000737:chemistry*; D006880:Hydroxy Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D054659:Diketopiperazines; D006880:Hydroxy Acids; D007769:Lactams; D011759:Pyrrolidines; C032519:pyrrolidine; C013165:statine