Cubane instead of benzene with the phenylethylamine backbone

Quote: Originally posted by Tellurium

Well synthesis of the cubane itself seems doable, but it requires quite some steps and especially a lot of reagents: https://www.synarchive.com/syn/14

I like this idea but im skeptical of cubanes ability to substitute benzene of all things due to it lacking any kind of resonance.

If we wanted to substitute cubane then we really dont need to look much further than the already planned synthesis.
After rearrangement of the final halo ketone, we are left with a carboxylic acid which would be our starting point for further substitutions.
For a phenethylamine backbone the carboxylic acid could be reduced to an aldehyde and then react this with hydrogen cyanide to form a hydroxynitrile. Followed by a reaction with thionyl chloride to form a halonitrile followed by a reaction with excess ammonia or the Gabriel synthesis and finally hydrolysis to form an amino acid.



This would be a good starting point for any other modifications we would like to make but i think just getting to an amino acid would be successful.
https://www.jstage.jst.go.jp/article/bcsj1926/63/8/63_8_2397...

With all this said, this is multi step organic synthesis and every step has a chance of something going wrong as well as decreasing our final yields drastically.
This is quite difficult practical research even for a well established laboratory with experience in this kind of thing.

Quote: Originally posted by Tsjerk

Quote: Originally posted by Tellurium   Well synthesis of the cubane itself seems doable, but it requires quite some steps and especially a lot of reagents: https://www.synarchive.com/syn/14 That looks pretty OTC! If one could do the first step in DCM instead of CCl4 and have SOCl2 on hand it is doable if you just aim on getting to the cubane backbone. I think loosing the carboxylic functional group is a waste anyway. One only needs to have a source of potassium terr-but oxide, but that shouldn't be that much of a problem. Acces to a NMR would also help, apparently the spectrum is very specific. [Edited on 28-12-2019 by Tsjerk]

Quote: Originally posted by Abromination

Quote: Originally posted by Tsjerk   Quote: Originally posted by Tellurium   Well synthesis of the cubane itself seems doable, but it requires quite some steps and especially a lot of reagents: https://www.synarchive.com/syn/14 That looks pretty OTC! If one could do the first step in DCM instead of CCl4 and have SOCl2 on hand it is doable if you just aim on getting to the cubane backbone. I think loosing the carboxylic functional group is a waste anyway. One only needs to have a source of potassium terr-but oxide, but that shouldn't be that much of a problem. Acces to a NMR would also help, apparently the spectrum is very specific. [Edited on 28-12-2019 by Tsjerk] If you use DCM as a solvent, remember that it can ignite in contact with the potassium t-butoxide.

Quote: Originally posted by Metacelsus

Quote: Originally posted by Abromination   Quote: Originally posted by Tsjerk   Quote: Originally posted by Tellurium   Well synthesis of the cubane itself seems doable, but it requires quite some steps and especially a lot of reagents: https://www.synarchive.com/syn/14 That looks pretty OTC! If one could do the first step in DCM instead of CCl4 and have SOCl2 on hand it is doable if you just aim on getting to the cubane backbone. I think loosing the carboxylic functional group is a waste anyway. One only needs to have a source of potassium terr-but oxide, but that shouldn't be that much of a problem. Acces to a NMR would also help, apparently the spectrum is very specific. [Edited on 28-12-2019 by Tsjerk] If you use DCM as a solvent, remember that it can ignite in contact with the potassium t-butoxide. I think you're confusing t-butyl peroxide with potassium t-butoxide. In the linked synthesis, potassium t-butoxide is not used.

Quote: Originally posted by Tsjerk

I'm thinking: Adipic acid + barium hydroxide = cyclopentanone cyclopentanone + ethylene glycol = Cyclopentanone ethylene ketal 1,4-dioxane* has been done and reported about here. Methanol, H2SO4, NaOH is all OTC. Bromine is easy as well. Ba(OH)2 I have, so I would only need adipic acid and a proper distillation setup. Also an UV LED would be needed, but those come cheap nowadays. * Nevermind, I can buy it. [Edited on 30-12-2019 by Tsjerk]