期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 6, 页码 2473-2480出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo402741g
关键词
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资金
- Program for Changjiang Scholars and Innovative Research Team in University [IRT13095]
- NSFC [21162034, 21372193, 21362040]
- Ministry of Education of China [20135301110002]
- Government of Yunnan Province [2012FB114, 2013FA026]
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.
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