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

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

Ruichao Shen  1 , Cheng Ting Lin, John A Porco Jr
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Total synthesis and stereochemical assignment of the salicylate antitumor macrolide lobatamide C(1)

Ruichao Shen et al. J Am Chem Soc. .

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.

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