Synthesis of 6-exomethylenepenams as beta-lactamase inhibitors

The 6,6-dibromopenam (6) was treated with CH3MgBr and carbaldehyde 5 to afford the hydroxy compound 7, which was reacted with acetic anhydride to give acetoxy compound 8. The deacetobromination of 8 with zinc and acetic acid gave 6-exomethylenepenams, E-isomer 10 and Z-isomer 9, which was oxidized t...

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Bibliographic Details
Published in:Archives of pharmacal research 1999-02, Vol.22 (1), p.68-71
Main Authors: Im, C, Oh, J S, Yim, C B
Format: Article
Language:English
Subjects:
beta-Lactamase Inhibitors
Chromatography, Thin Layer
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Magnetic Resonance Spectroscopy
Penicillins - chemical synthesis
Penicillins - chemistry
Spectrophotometry, Ultraviolet
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Summary:The 6,6-dibromopenam (6) was treated with CH3MgBr and carbaldehyde 5 to afford the hydroxy compound 7, which was reacted with acetic anhydride to give acetoxy compound 8. The deacetobromination of 8 with zinc and acetic acid gave 6-exomethylenepenams, E-isomer 10 and Z-isomer 9, which was oxidized to sulfone 11 by m-CPBA. The p-methoxybenzyl compounds were deprotected by AlCl3 and neutralized to give the sodium salts 12, 13 and 14.
ISSN:0253-6269
1976-3786
DOI:10.1007/BF02976438