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Total synthesis and stereochemical assignment of the salicylate antitumor macrolide lobatamide C(1)
Ruichao Shen1, Cheng Ting Lin, John A Porco
1Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, Boston University, Boston, Massachusetts 02215, USA.
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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