Total syntheses of several types of racemic 1-carbacephem derivatives, 30, 32, 35, 37, 39, 45, 46, 50, 56, 57, 58, 65, and preliminary biological results are described. Addition of azidoacetyl chloride to the Schiff base 10 in the presence of triethylamine gave cis-azetidinones 11a, b which were converted to the racemic key intermediate 5. By applying sequences of reactions developed in 1-oxacephem syntheses, various kinds of 1-carbacephems were prepared from 5. Among twelve derivatives prepared, 50 showed the highest antibacterial activity.
本文介绍了几种外消旋 1-卡巴西姆衍
生物 30、32、35、37、39、45、46、50、56、57、58 和 65 的全合成方法和初步
生物学结果。在
三乙胺存在下,将
叠氮乙酰氯加到希夫碱 10 上,可得到顺式氮杂
环丁酮 11a、b,并将其转化为外消旋关键中间体 5。通过应用在 1-氧杂
环丁烷合成中开发的反应序列,从 5 制备出了各种 1-氧杂
环丁烷。