Total synthesis and stereochemical assignment of the salicylate antitumor macrolide lobatamide C(1).
Total synthesis and stereochemical assignment of the salicylate antitumor macrolide lobatamide C(1).
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DOI：
10.1021/ja026025a
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发表时间：
2002-04
影响因子：
15
通讯作者：
R. Shen;C. Lin;J. Porco
中科院分区：
文献类型：
--
作者：
R. Shen;C. Lin;J. Porco
报道了抗肿瘤大环内酯类化合物洛巴他胺C的全合成及立体化学归属。该合成涉及Cu（I）介导的烯酰胺形成和Na（2）CO（3）介导的β-羟基酸和水杨酸氰基甲酯的酯化。使用Mitsunobu方案完成大环内酯化。通过Mosher酯分析和与制备的立体异构体的比较，实现了洛巴他胺C的立体化学归属。
The total synthesis and stereochemical assignment of the potent antitumor macrolide lobatamide C is reported. The synthesis involves Cu(I)-mediated enamide formation and Na(2)CO(3)-mediated esterification of a beta-hydroxy acid and a salicylate cyanomethyl ester. Macrolactonization was accomplished using a Mitsunobu protocol. The stereochemical assignment of lobatamide C was achieved by Mosher ester analysis and comparison with prepared stereoisomers.