Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine

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Title

Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine

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The University of Auckland Library

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ResearchSpace@Auckland

Description

Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxyamphimedine, deoxyamphimedine, and amphimedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, with paraformaldehyde afforded demethyldeoxyamphimedine and deoxyamphimedine. Oxidation of the latter using either K3[Fe(CN)6] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the met...

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Format

Research paper

Research format

Journal article

Date created

2015-12-07

Creator

Khalil, IM / Barker, David / Copp, Brent

URL

http://hdl.handle.net/2292/34510

Related subjects

Alkaloids / Acridines / Phenanthrolines / Biological Products / Molecular Structure

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