摘要 |
PURPOSE: To easily and effectively obtain a 2-vinyl-substituted carbapenem derivative useful as a β-lactam antibiotic substance under mild reaction condition by directly introducing a substituted vinyl group at a specific site of a carbapenem skeleton. CONSTITUTION: The objective derivative of formula I [R is a carbapenem skeleton; R<4> and R<5> are each H or a residue; R<4> and R<5> may together form a carbon ring), e.g. p-methoxybenzyl (1S,5R,6S)-2-[(E)-3-(p-methoxybenzyloxycarbonyl) amino-1-propen-1-yl]-1-methyl-6-[(1R)-1-(triethylsiloxy)ethyl]carbapen -2-em-3- carboxylate is produced by reacting (A) a carbapenem compound of formula R-Z having an eliminable substituent Z on the 2-site (preferably Z is a halogeno- lower alkanesulfonic acid group, etc.) with (B) a 1-olefin compound of formula II in an organic solvent in the presence of a palladium catalyst [preferably bis(dibenzylideneacetone)palladium(0), etc.]. |