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

共 69 条

[1] β-lactams as versatile synthetic intermediates for the preparation of heterocycles of biological interest [J].

Alcaide, B ;

Almendros, P .

CURRENT MEDICINAL CHEMISTRY, 2004, 11 (14) :1921-1949

[2] Recent advances in the stereocontrolled synthesis of bi- and tricyclic-β-lactams with non-classical structure [J].

Alcaide, B ;

Almendros, P .

CURRENT ORGANIC CHEMISTRY, 2002, 6 (03) :245-264

[3]

Alcaide B, 2002, SYNLETT, P381

[4] PREPARATION OF ALPHA-METHYLENE AND ALPHA-ETHYLIDENE BETA-LACTAMS VIA THE ESTER ENOLATE IMINE CONDENSATION USING BETA-(DIALKYLAMINO) ESTERS AS STARTING MATERIALS - SCOPE AND SYNTHETIC APPLICATIONS [J].

ALCAIDE, B ;

ESTEBAN, G ;

MARTINCANTALEJO, Y ;

PLUMET, J ;

RODRIGUEZLOPEZ, J ;

MONGE, A ;

PEREZGARCIA, V .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :7994-8002

[5] Stereoselective synthesis of fused bicyclic β-lactams through radical cyclization of enyne-2-azetidinones [J].

Alcaide, B ;

Rodríguez-Campos, IM ;

Rodríguez-López, J ;

Rodríguez-Vicente, A .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5377-5387

[6] Stereoselective NaN3-catalyzed halonitroaldol-type reaction of azetidine-2,3-diones in aqueous media [J].

Alcaide, Benito ;

Almendros, Pedro ;

Luna, Amparo ;

Torres, M. Rosario .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) :1635-1640

[7] Metal-catalyzed regiodivergent cyclization of γ-allenols:: Tetrahydrofurans versus oxepanes [J].

Alcaide, Benito ;

Almendros, Pedro ;

del Campo, Teresa Martinez .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (35) :6684-6687

[8] β-lactams:: Versatile building blocks for the stereoselective synthesis of non-β-lactam products [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMICAL REVIEWS, 2007, 107 (11) :4437-4492

[9] Synthesis of Fused-β-Lactams through Selective Gold-Catalyzed Oxycyclization of Dioxolane-Tethered Enynes [J].

Alcaide, Benito ;

Almendros, Pedro ;

Martinez del Campo, Teresa ;

Rosario Torres, M. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) :8956-8965

[10] Metal-Catalyzed Cycloisomerization and Tandem Oxycyclization/Hydroxylation of Alkynols: Synthesis of Nonfused, Spiranic and Fused Oxabicyclic β-Lactams [J].

Alcaide, Benito ;

Almendros, Pedro ;

Martinez del Campo, Teresa ;

Carrascosa, Rocio .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (25) :4912-4919

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