Synthesis of 6-exomethylenepenams as beta-lactamase inhibitors

Authors
Im, C Oh, JS Yim, CB
Citation
C. Im et al., Synthesis of 6-exomethylenepenams as beta-lactamase inhibitors, ARCH PH RES, 22(1), 1999, pp. 68-71
Citations number
11
Categorie Soggetti
Pharmacology & Toxicology
Journal title
ARCHIVES OF PHARMACAL RESEARCH
ISSN journal
02536269 → ACNP
Volume
22
Issue
1
Year of publication
1999
Pages
68 - 71
Database
ISI
SICI code
0253-6269(199902)22:1<68:SO6ABI>2.0.ZU;2-6
Abstract
The 6,6-dibromopenam (6) was treated with CH3MgBr and carbaldehyde 5 to aff ord 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 o sulfone 11 by m-CPBA. The p-methoxybenzyl compounds were deprotected by A lCl3 and neutralized to give the sodium salts 12, 13 and 14.