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

Nicola Piens (UGent) , Sven De Craene, Jorick Franceus (UGent) , Karen Mollet (UGent) , Kristof Van Hecke (UGent) , Tom Desmet (UGent) and Matthias D'hooghe (UGent)
(2016) ORGANIC & BIOMOLECULAR CHEMISTRY. 14(47). p.11279-11288
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Abstract
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.
Keywords
STRUCTURE-BASED DESIGN, STEREOSELECTIVE-SYNTHESIS, ASYMMETRIC-SYNTHESIS, RADICAL CYCLIZATION, BUILDING-BLOCKS, STEREOCONTROLLED SYNTHESIS, STEREOSPECIFIC SYNTHESIS, STAUDINGER REACTION, GAMMA-ALLENOLS, ANTIBIOTICS

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Chicago
Piens, Nicola, Sven De Craene, Jorick Franceus, Karen Mollet, Kristof Van Hecke, Tom Desmet, and Matthias D’hooghe. 2016. “Diastereoselective Synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and Their Transformation into 3,4-oxolane-fused Bicyclic Β-lactams.” Organic & Biomolecular Chemistry 14 (47): 11279–11288.
APA
Piens, N., De Craene, S., Franceus, J., Mollet, K., Van Hecke, K., Desmet, T., & D’hooghe, M. (2016). Diastereoselective synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation into 3,4-oxolane-fused bicyclic β-lactams. ORGANIC & BIOMOLECULAR CHEMISTRY, 14(47), 11279–11288.
Vancouver
1.
Piens N, De Craene S, Franceus J, Mollet K, Van Hecke K, Desmet T, et al. Diastereoselective synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation into 3,4-oxolane-fused bicyclic β-lactams. ORGANIC & BIOMOLECULAR CHEMISTRY. 2016;14(47):11279–88.
MLA
Piens, Nicola et al. “Diastereoselective Synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and Their Transformation into 3,4-oxolane-fused Bicyclic Β-lactams.” ORGANIC & BIOMOLECULAR CHEMISTRY 14.47 (2016): 11279–11288. Print.
@article{8198531,
  abstract     = {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.},
  author       = {Piens, Nicola and De Craene, Sven and Franceus, Jorick and Mollet, Karen and Van Hecke, Kristof and Desmet, Tom and D'hooghe, Matthias},
  issn         = {1477-0520},
  journal      = {ORGANIC & BIOMOLECULAR CHEMISTRY},
  keywords     = {STRUCTURE-BASED DESIGN,STEREOSELECTIVE-SYNTHESIS,ASYMMETRIC-SYNTHESIS,RADICAL CYCLIZATION,BUILDING-BLOCKS,STEREOCONTROLLED SYNTHESIS,STEREOSPECIFIC SYNTHESIS,STAUDINGER REACTION,GAMMA-ALLENOLS,ANTIBIOTICS},
  language     = {eng},
  number       = {47},
  pages        = {11279--11288},
  title        = {Diastereoselective synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation into 3,4-oxolane-fused bicyclic β-lactams},
  url          = {http://dx.doi.org/10.1039/c6ob02221a},
  volume       = {14},
  year         = {2016},
}

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