Diastereoselective synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation into 3,4-oxolane-fused bicyclic β-lactams

被引：12

作者：

Piens, Nicola ^{[1
]}

De Craene, Sven ^{[1
]}

Franceus, Jorick ^{[2
]}

Mollet, Karen ^{[1
]}

Van Hecke, Kristof ^{[3
]}

Desmet, Tom ^{[2
]}

D'hooghe, Matthias ^{[1
]}

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Sustainable Organ Chem & Technol, SynBioC Res Grp, Coupure Links 653, B-9000 Ghent, Belgium

[2] Univ Ghent, Fac Biosci Engn, Dept Biochem & Microbial Technol, Coupure Links 653, B-9000 Ghent, Belgium

[3] Univ Ghent, Fac Sci, Dept Inorgan & Phys Chem, XStruct, B-9000 Ghent, Belgium

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 47期

基金：

比利时弗兰德研究基金会;

关键词：

STRUCTURE-BASED DESIGN; STEREOSELECTIVE-SYNTHESIS; BUILDING-BLOCKS; ASYMMETRIC-SYNTHESIS; RADICAL CYCLIZATION; STEREOSPECIFIC SYNTHESIS; GAMMA-ALLENOLS; ANTIBIOTICS; INHIBITORS; TETRAHYDROFURAN;

D O I：

10.1039/c6ob02221a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

cis-3-Acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones were prepared through a Staudinger [2+2]-cyclo-condensation between acetoxyketene and the appropriate epoxyimines in a highly diastereoselective way. Subsequent potassium carbonate-mediated acetate hydrolysis, followed by intramolecular ring closure through epoxide ring opening, afforded stereodefined 3-aryl-4-hydroxy-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones as a novel class of C-fused bicyclic beta-lactams. Selective benzylic oxidation of bicyclic N-(4-methoxybenzyl)-beta-lactams with potassium persulfate and potassium dihydrogen phosphate provided the corresponding N-aroyl derivatives as interesting leads for further beta-tactamase inhibitor development.

引用

页码：11279 / 11288

页数：10

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