Total synthesis of (-)-tetrazomine. Determination of the stereochemistry of tetrazomine and the synthesis and biological activity of tetrazomine analogues
Total synthesis of (-)-tetrazomine. Determination of the stereochemistry of tetrazomine and the synthesis and biological activity of tetrazomine analogues
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DOI：
10.1021/ja0174027
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发表时间：
2002-03-27
影响因子：
15
通讯作者：
Williams, RM
中科院分区：
文献类型：
--
作者：
Scott, JD;Williams, RM
强效抗肿瘤抗生素（-）-四唑胺的首次全合成已经完成。一种用于形成偶氮甲碱叶立德的烯丙胺前体的新方法已被开发并用于有效的[1,3]-偶极环加成，以提供用于合成(-)-四唑胺的关键四环中间体。已经合成了四唑明的几种类似物并测试了其抗菌和生化活性。
The first total synthesis of the potent antitumor antibiotic (-)-tetrazomine has been accomplished. A new method for the formation of the allylic amine precursor to an azomethine ylide has been developed and exploited in an efficient [1,3]-dipolar cycloaddition to afford the key tetracyclic intermediate used in the synthesis of (-)-tetrazomine. Several analogues of tetrazomine have been synthesized and tested for antimicrobial and biochemical activity.