A concise synthesis of the Lycopodium alkaloid cermizine D
TETRAHEDRON LETTERS（2015）
Abstract
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. (C) 2015 Elsevier Ltd. All rights reserved.
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Key words
Alkaloid synthesis,Lycopodium alkaloids,Nitrogen heterocycles,1-Acylpyridinium salts,Asymmetric synthesis
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