Shen Ruichao, Lin Cheng Ting, Porco John A
Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, Boston University, Boston, Massachusetts 02215, USA.
J Am Chem Soc. 2002 May 22;124(20):5650-1. doi: 10.1021/ja026025a.
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.