NEW ROUTES TO a-AMINO ACID b,g-THIOENOL ETHER DERIVATIVES

Patrick Meffre (1) , Patrick Mcffrc , Philippe Durand (2)

1 ENSCP - Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL
2 CCD - Communications Cellulaires et Différenciation

Racemic derivatives of C'J.-amino acid 13.y-lhioenol ethL'rs have been synthesized rrom homoserine through a y-climination on a sulfoxidc deri,ed f' rom aspart:ddchydc. Optically aeti\' c deri­ vatives were clTieicntly prepared rrom /.-methionine by a Pummerer like reaction. Y.-/\mino acid B.y-cnol ethers I and their sulf' ur analogues 2 arc com­ pounds or biological interest: they arc possible pyridoxal phosphate depen­ dent enzyme inhibitors because of the prescrn:c or the double bond in the B.y-position. 1 Indeed. the oxygen analogues 1 have shown antibiotic :' ,etivity. 2 Both types of compounds exhibit somc antiproliferatiw activity bccause they a<.:t as methionine analogues and inhibit S-adenosyl methionine translcrase.; (Scheme I)

Domaines: Chimie; Chimie organique

Patrick Meffre, Patrick Mcffrc, Philippe Durand. NEW ROUTES TO a-AMINO ACID b,g-THIOENOL ETHER DERIVATIVES. Synthetic Communications, 2006, 32 (2), pp.287-296. ⟨hal-02002695⟩