Total synthesis and stereochemical assignment of the salicylate antitumor macrolide lobatamide C(1).
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.
Shen
Ruichao
R
Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, Boston University, Boston, Massachusetts 02215, USA.
Lin
Cheng Ting
CT
Porco
John A
JA
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D012459:Salicylates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D018942:Macrolides; D012459:Salicylates; C460781:lobatamide C