Journal of Organic Chemistry
Journal of Organic Chemistry
3 years ago

Total Synthesis of (±)-Cermizine B

Total Synthesis of (±)-Cermizine B
Yu Zhu, Xin Shi, Li-Dong Shao, Ying Bao, Zhen-Tao Deng, Qin-Shi Zhao
A practical synthesis of (±)-cermizine B was achieved. The nine-step synthesis mainly comprised two uninterrupted Michael additions including a highly diastereoselective 1,4-addition of 2-picoline to methyl 4-methyl-6-oxocyclohex-1-ene-1-carboxylate, Krapcho decarboxylation, a double reductive amination that resulted in ring closure and dearomatization of pyridine in 24% overall yield.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02073

DOI: 10.1021/acs.joc.7b02073

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