SIMPLE AND CONDENSED BETA-LACTAMS .5. THE SYNTHESIS OF SOME (5RS,6SR)-2-(2-FORMYLAMINOETHYLTHIO)-6-(2-METHYL-1,3-DIOXOLAN-2-YL)CARBAPENEM-3-CARBOXYLIC ACID-DERIVATIVES AND RELATED-COMPOUNDS
SIMPLE AND CONDENSED BETA-LACTAMS .5. THE SYNTHESIS OF SOME (5RS,6SR)-2-(2-FORMYLAMINOETHYLTHIO)-6-(2-METHYL-1,3-DIOXOLAN-2-YL)CARBAPENEM-3-CARBOXYLIC ACID-DERIVATIVES AND RELATED-COMPOUNDS
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DOI：
10.1039/p19860000221
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发表时间：
1986-02-01
期刊：
影响因子：
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通讯作者：
DOLESCHALL, G
中科院分区：
文献类型：
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作者：
FETTER, J;LEMPERT, K;DOLESCHALL, G
从4-氧代氮杂环丁烷-2-羧酸（3a）和（3b）开始，已经开发了用于合成外消旋碳青霉烯-3-羧酸（2）的衍生物的方法，所述碳青霉烯-3-羧酸（2）是有效抗生素硫霉素的类似物。合成步骤包括通过Araben-Schirtert和Masamune的方法进行的链延长、重氮基团转移、N-保护的2，4-二甲氧基苄基和对甲氧基苯基的氧化去除、涉及卡宾插入反应的环化、以及通过烯醇磷酸酯活化将双环化合物（13 b）的酮部分转化为烯乙基部分。目标化合物钠盐（14 c）不具有任何有用的生物活性。
Starting with the 4-oxoazetidine-2-carboxylic acids (3a) and (3b), methods for the synthesis of derivatives of the racemic carbapenem-3-carboxylic acid (2), an analogue of the potent antibiotic thienamycin have been developed. The synthetic steps included chain elongations by the methods of Arndt-Eistert and Masamune, diazo group transfers, oxidative removals of N-protecting 2,4-dimethoxybenzyl and p-methoxyphenyl groups, cyclization involving a carbene insertion reaction, and conversion of the ketone moiety of the bicyclic compound (13b) into an enethiol moiety via enolphosphate activation. The target compound, the sodium salt (14c) did not possess any useful biological activity.