Total Synthesis Blog

This sunday, very simple target molecule – aplysamine 6 which shows inhibition aganist isopropenylcysteine carboxy methyl transferase (Icmt), which is important in oncogenesis. The structure of aplysamine 6 is drawn below:

Let me add that aplysamine 6 is a natural product (of course) isolated from sponge Pseudoceratina sp.

Well, that’s not very complex target and the retrosynthesis and also total synthesis should be quite easy. My idea to disconnect this stuff is something like that:

Read the rest of this entry »

Do you know snowdrops? It’s well-known that bulbs of these flowers (latin name is Galanthus nivalis) contain many alkaloids and galantamine (or galanthamine) is one of them:

This is an important natural product because of its biological properties and phamacological applications – it’s used in treatment of mild Alzheimer’s disease. So there are many approaches to total synthesis of galantamine and here I’ll try to show most recent of them (I think so).

Authors of the paper on which I base developed new interesting reaction: DMCRC – what means Double Michael-Claisen Reaction Cascade. The reaction allows to synthesise quickly highly substituted cyclohexenones which can be used in total syntheses of many ’sterically congested’ natural products and galantamine is only one of several examples mentioned in paper (the others are aspidospermidone, lycoramine and  mesembrine).

Let’s look at retrosynthetic analysis:

Read the rest of this entry »