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Total synthesis and stereochemical assignment of the salicylate antitumor macrolide lobatamide C(1).

作者信息

Shen Ruichao, Lin Cheng Ting, Porco John A

机构信息

Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, Boston University, Boston, Massachusetts 02215, USA.

出版信息

J Am Chem Soc. 2002 May 22;124(20):5650-1. doi: 10.1021/ja026025a.

Abstract

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.

摘要

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