Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A Simple Synthesis of Amphimedine

RH Prager, C Tsopelas and T Heisler

Australian Journal of Chemistry 44(2) 277 - 285
Published: 1991

Abstract

The marine alkaloid amphimedine has been synthesized by a short sequence of reactions commencing from the known indenopyridinedione (2). Reaction with 4-pyridyllithium, followed by hydrazoic acid treatment, gave 5-(4-pyridyl)-3,6-phenanthrolin-4(3H)-one (12) which was converted into the chlorophenanthroline. The methyl-substituted fluorosulfonate salt of this compound was specifically oxidized by alkaline ferricyanide. Conversion of the pyridone into the nitrile gave the precursor which was cyclized to amphimedine by polyphosphoric acid.

https://doi.org/10.1071/CH9910277

© CSIRO 1991


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