Journal
TETRAHEDRON LETTERS
Volume 56, Issue 23, Pages 3683-3685Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.04.013
Keywords
Alkaloid synthesis; Lycopodium alkaloids; Nitrogen heterocycles; 1-Acylpyridinium salts; Asymmetric synthesis
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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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