1572571-98-2Relevant academic research and scientific papers
Catalytic enantioselective and divergent total synthesis of (+)-10-oxocylindrocarpidine, (+)-cylindrocarpidine, (-)- N - acetylcylindrocarpinol, and (+)-aspidospermine
Shen, Xiao-Lei,Zhao, Rui-Rui,Mo, Ming-Jie,Peng, Fang-Zhi,Zhang, Hong-Bin,Shao, Zhi-Hui
, p. 2473 - 2480 (2014/04/17)
The catalytic enantioselective and divergent total syntheses of Aspidosperma alkaloids (+)-10-oxocylindrocarpidine 7, (+)-cylindrocarpidine 1, (-)-N-acetylcylindrocarpinol 6, and (+)-aspidospermine 8 have been accomplished in 11 steps from a common precursor (15) on the basis of a highly concise route. The route features three metal-catalyzed reactions, including the key Pd-catalyzed decarboxylative asymmetric allylation of carbazolones developed in our laboratory. Our syntheses, using a combination of C-H activation, enantioselective catalysis, and collective synthesis, represent the first total synthesis of 10-oxocylindrocarpidine and the first asymmetric total synthesis of cylindrocarpidine and N-acetylcylindrocarpinol.
