A gold(I)-catalysed approach towards harmalidine an elusive alkaloid from Peganum harmala

[murklan]

Getting closer to alchemy?

A gold(I)-catalysed approach towards harmalidine an elusive alkaloid from Peganum harmala

But the process seems really complicated and I don't even know if the molecules are in any way psychoactive. Just didn't know gold was used in catalyzing.

 

[downwardsfromzero]

Interesting, but neither accessible nor relevant to the average harmala enthusiast!

The gold has phosphine ligands, the starting material is an alkynyl azetidine, and it's not clear what the harmalidine would be useful for.

Gold-catalysed rearrangement: from N-3-methoxyphenyl alk-1-ynyldimethylazetidine C to pyrrolo[1,2-a]indole B

With these azetidines in hand, the gold-catalysed rearrangement was studied. Under our precedent optimized conditions,16 the expected 2,3-dihydropyrrolo[1,2-a]indoles were readily obtained but in modest yields due to some degradation. A brief condition screening revealed that 2-biphenyldicyclohexylphosphino-gold(I) hexafluoroantimonate was still the best catalyst but 1,2-dichloroethane (DCE) turned out to be better as solvent, while refluxing minimized degradation due to short reaction times.

Condensation of an alkyne with a substituted aniline is a common strategy in indole synthesis.

 

[murklan]

I don't understand any of it, but the field of chemistry is certainly interesting. And with a language for all those processes.

I've seen somewhere how the amount of man-made chemicals has increased enormously the last 120 years. That is magic, for good and bad I think.

 

[downwardsfromzero]

If it's alchemy you want, stuff like Wilkinson's catalyst and its palladium and iridium analogues are also verging on magical.