67.Total Synthesis of (±)-Decinine via an Oxidative Biaryl Coupling with Defined Axial Chirality-YANG Group

67.Total Synthesis of (±)-Decinine via an Oxidative Biaryl Coupling with Defined Axial Chirality

Zhen-Hua Shan, Ji Liu, Ling-Min Xu, Ye-Feng Tang, Jia-Hua Chen, and Zhen Yang

Org. Lett. 2012, 14, 3712

The total synthesis of (±)-decinine has been achieved. The key steps in the synthesis involved the formation of lasubine II via a gold catalyzed annulation of 1-(but-3-yn-1-yl)piperidine and the formation of the 12-membered ring of decinine (1) with complementary atropselectivity via a VOF3-mediated oxidative biaryl coupling reaction.