Synthesis of 4-vinyl substituted β-lactams of the oxamazin family

✍ Scribed by Giuseppe Guanti; Eva Baldaro; Luca Banfi; Alberto Guaragna; Enrica Narisano; Umberto Valcavi

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 633 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)85998-6

✦ Synopsis

4-~nyl-sub~~ed oxamazlns lb, 16, and 3 have beefI prepared. Key steps of the synthesis are: the preparation of protected a-amino-)I-hydroxyadd 6 through ester enolate condensation of ethyl glycinate STABASE addwt 8 with W-protected pfopiotatdehyde 9, the coupling of this acid with an appropriate protected hydroxylamine, the cyclirationof resulting hydroxamale, and finally the acylation of the amtnogfoup in 3 with AX440 side chain. The discovery of the fnonobactams 11 (Scheme l), a new class of amibiottcs panicularty active against gram negattve bauerta, has stimulated a lively interest in the synthesis of novel monocyctic S&cWns. More recently it was found that good to potent antibiotic activities could be still achieved by substituting the SOg-moiety with other eie~ron.withd~wi~ groups,* like for exampie in oxamaains ot general toffnula 2.3:4