2015 journal article
A concise synthesis of the Lycopodium alkaloid cermizine D
TETRAHEDRON LETTERS, 56(23), 3683–3685.
author keywords: Alkaloid synthesis; Lycopodium alkaloids; Nitrogen heterocycles; 1-Acylpyridinium salts; Asymmetric synthesis
open access via manuscript.elsevier.com (publisher PDF)
UN Sustainable Development Goal Categories
3. Good Health and Well-being
(Web of Science)
Source: Web Of Science
Added: August 6, 2018
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.