Total synthesis of the proposed structure of metacridamide B

Abstract The first asymmetric total synthesis of the proposed structure of metacridamide B, a 17-membered macrolide with anticancer activity, has been accomplished in a highly convergent and flexible manner. The key features of our synthesis involved hydroxyl directed ruthenium catalyzed alkyne functionalization, Stille coupling, asymmetric Corey-Bakshi-Shibata reduction, Micalizio coupling and Yamaguchi macrolactonization. Careful comparison of the 1H and 13C NMR spectroscopic data confirmed that the natural metacridamide B had been erroneously represented as its C9-epimer.