Synthesis of Plicamine

Abstract

The Amaryllidaceae alkaloids have become targets for synthetic chemists, due to their wide variety of bioactivities and potential for utilization in medicinal chemistry. In addition, the structural complexity of these alkaloids makes them interesting and challenging to synthesize and most of them are classified as isoquinoline alkaloids, whose structures are often different. The study showed that it was formed biogenetically by intramolecular oxidative coupling of norbelladines. At present, there is an isolation of Amaryllidaceae alkaloids from more than 100 plants and through spectroscopic structure determination.

At present, our research group is studying the synthesis of natural products in the indolizidine, quinolizidine, and other related alkaloids, including isoquinoline alkaloids, using chiral succinimide and chiral glutarimide as key intermediates in the synthesis, both of which are synthesized from L-amino acid.

In this research, we will discuss synthetic studies of plicamine, which are not classified as indolizidine or quinolizidine alkaloids but could be synthesized using chiral dibenzylamino-succinimide as a key intermediate as well.

Plicamine is an Amaryllidaceae alkaloid isolated by Manfred’s research group in 1999 from Galanthus plicatus subsp. byzantinus, a plant native to northwestern Turkey. Moreover, plicamine possesses in vitro anti-inflammatory activity by the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production.

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