[Rictiovarus]

Hello everyone!

I have been working on this synthesis proposal and have reached a step where I would like to do an epimerization:
https://prnt.sc/rskzik

I've been looking at literature on epimerization reactions in organic synthesis but have been struggling to understand them as well as I would like. Is anyone able to help me understand a bit how I can epimerize a carbon with an acidic carbon like this? From what I understand a catalyst may or may not be required?

Thank you

[Babcock_Hall]

Rictovarus,

It is a forum rule (see red link above) that you must show your attempt or give your thoughts before we can help you.  What sort of a catalyst do you have in mind?

[Rictiovarus]

Rictovarus,

It is a forum rule (see red link above) that you must show your attempt or give your thoughts before we can help you.  What sort of a catalyst do you have in mind?

That's the issue, I'm having a particularly difficult time finding relevant literature. This is the sort of reaction I am looking to accomplish: http://www.ochempal.org/index.php/alphabetical/e-f/epimerization/.
Without a catalyst, from what I can gauge, simple deprotonation and re-protonation would yield the same diastereomer as the proton will selectively come in from the back of the molecule.
I have tried to illustrate, to the best of my abilities, a better illustration of my molecule, with a red dot signifying toe position I want to epimerize: https://prnt.sc/rt58pa.

I understand it isn't much and that's because I don't have much. What I am looking for really is advice on how I could go about starting this or a better way to search for relevant literature. I would do another search on SciFinder if it weren't down at the moment. I understand if nobody can help me since I don't have a proper attempt.

[Babcock_Hall]

I think that you are making an assumption that is not necessarily true.  There are enzymes that are epimerases.  One that comes to mind is the one that interconverts D and L methylmalonyl CoA.  I am not suggesting that an enzyme is necessary here, only that you think about what the existence of what such enzymes implies.