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化学学报
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化学学报 ›› 1956, Vol. 22 ›› Issue (4): 264-270. 上一篇    下一篇

论文

金黴素的隣羟甲基苯甲酸内酯類降解物的同型物的合成

蔣明謙1,2, 李光亮1, 李廣年1, 任新民1   

  1. 1. 中国科学院有机化学研究所;
    2. 北京医学院药学系
  • 投稿日期:1956-04-10 发布日期:2013-06-04

SYNTHESIS OF ANALOGS OF PHTHALIDYL DEGRADATION PRODUCTS OF AUREOMYCIN

CHIAN MIN-CHINE1,2, LEE KWANG-LIANG1, LEE KWANG-NINE1, JEN HSIN-MIN1   

  1. 1. Institute of Organic Chemistry, Academia Sinica;
    2. Department of Pharmacy, Peking Medical College
  • Received:1956-04-10 Published:2013-06-04

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本文试图合成黴素的隣羟甲基苯甲酸内酯類降解物的近似同型物.已合成3-(3-甲基隣羟甲基苯甲酸内酯基)-苄基丙二酸乙酯(IXA)和3-(3-甲基隣羥甲基苯甲酸内酯基)-(3',5'-二甲氧基苄基)-丙二酸乙酯(IXB).也曾试图合成3-(3-甲基-4-氯-7-甲氧基隣羟甲基苯甲酸内酯基)-(3',5'-二甲氧基苄基)-丙二酸乙酯(IXC),但未得到纯产物.化合物IXA和IXB不能用酸使其水解.前者也不能被氫氧化銨,氫氧化鋇等鹼水解,但對於氫氧化鈉或氫氧化鉀却十分敏感,與1N或0.2N强鹼溶液共熱卽能破裂而得到隣乙醯苯甲酸.1N氫氧化鈉溶液也能破坏化合物IXB.

For the purpose of synthesis of desdimethylaminoaureomycinic acid(Ⅵ), one of the main degradation products of aureomycin, some close analogs were first prcpared.By means of the method of Bothe and coworkers, we synthesized some compounds of the general formula Ⅸ, which were then subjected to hydrolysis and decarboxylation in ordcr to get the corresponding acid Ⅹ.Through chain-lengthening processes, Ⅹ might be transformed into the desired analogs of Ⅵ.