Details

Autor(en) / Beteiligte

• Shen, Xiao-Lei
• Zhao, Rui-Rui
• Mo, Ming-Jie
• Peng, Fang-Zhi
• Zhang, Hong-Bin
• Shao, Zhi-Hui

Titel

Catalytic Enantioselective and Divergent Total Synthesis of (+)-10-Oxocylindrocarpidine, (+)-Cylindrocarpidine, (−)‑N‑Acetylcylindrocarpinol, and (+)-Aspidospermine

Ist Teil von

• Journal of organic chemistry, 2014-03, Vol.79 (6), p.2473-2480

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2014

Quelle

MEDLINE

Beschreibungen/Notizen

• 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.