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