A concise synthesis of the Lycopodium alkaloid cermizine D

作者：Enamorado Monica F; Connelly Colleen M; Deiters Alexander; Comins Daniel L^*

来源：Tetrahedron Letters, 2015, 56(23): 3683-3685.

DOI：10.1016/j.tetlet.2015.04.013

• Alkaloid synthesis
• Lycopodium alkaloids
• Nitrogen heterocycles
• 1-Acylpyridinium salts
• Asymmetric synthesis

A racemic and asymmetric synthesis of cermizine D (1) was accomplished in six steps from 4-methoxypyridine or 4-methoxy-3-TIPS-pyridine in 12% and 13% overall yield, respectively. A key step is a stereoselective 1,4-addition of a 2-((trimethylsilyl)methyl)pyridine-derived cuprate to a bicyclic 2,3-dihydro-4-pyridone. Racemic and (-)-cermizine D failed to exhibit cytotoxicity against four different cell lines.

• 出版日期2015-6-3