[chloec]

I'm an undergraduate in third year and am really struggling with a retrosynthesis of some molecules, they have never been officially retrosynthesised reasonably, we just need to attempt to give 2 appropriate forward synthesis for each. I was hoping someone could help me because my books and notes and knowledge aren't helping much at all. I have 3 molecules and I know thats a lot but even helping with one will help me in the right direction:

1. Montipyridine (i was thinking RCM maybe?)
2. Eutypinol (transferring the alkyne back to an alkene then maybe removing the OH, but then I'm stuck)
3. Meridianin A (absolutely stumped on this one)

Thanks to anyone who can help I will really appreciate it! If you need a photo of the molecules in case they are tricky to find on google I'll post them up.
             

[kriggy]

Can you post how actualy the molecules look like? I found only one on google

[sjb]

Can you post how actualy the molecules look like? I found only one on google

• Montipyridine (i was thinking RCM maybe?) - http://dx.doi.org/10.1021/np0100892?
• Eutypinol http://www.molecular-networks.com/biopath3/biopath/mols/Eutypinol?
• Meridianin A http://dx.doi.org/10.2174/138955712800626728?

edit html typo

[chloec]

I have uploaded the other 2 for you, thank you so much! I have tried accessing that scientific journal for the montipyridine but have failed so far so I'm contacting various websites and the editor of the journal and hoping for some feedback.

[kriggy]

Ok what about this?
If you look at the one of the molecules lets say montipyridine you should try to indentify molecule or structure which was direct precursor for the one you have and then continue doing the same for the precursors until you find a compound which you have / can buy / can preparea easily.
So for the montipiridine I did this:
There is pyridine, acetic acid, nonen chain and methoxy group.
So I did start with methoxy group and found out that you can use williamson ether synthesis using 4-hydroxypyridine and chlormethan and later found out that you can even buy methoxypyridine at sigma. And then you can continue..

[orgopete]

I would consider a condensation reaction between guanidine and a keto-aldehyde. It then looks like predictable chemistry to prepare and react an indole to make said intermediate.

[kriggy]

why would you make the condensation if you can get both reagents from sigma? Or am I missing something?

[chloec]

Sorry for such a long wait in my reply I haven't had access to my laptop. Thank you so much! I've never been taught that way of retrosynthesis, as in looking at what molecules exist in it already, more so the reasonable cleavages. Thank you again I really appreciate your help