2015 journal article

A concise synthesis of the Lycopodium alkaloid cermizine D

TETRAHEDRON LETTERS, 56(23), 3683–3685.

By: M. Enamorado n, C. Connelly n, A. Deiters n & D. Comins n

co-author countries: United States of America πŸ‡ΊπŸ‡Έ
author keywords: Alkaloid synthesis; Lycopodium alkaloids; Nitrogen heterocycles; 1-Acylpyridinium salts; Asymmetric synthesis
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 (βˆ’)-cermizine D failed to exhibit cytotoxicity against four different cell lines.