[confusedug45]

So I believe the 1-(lithiooxy)-1-methoxyethene is acting either as a base or as a soft nucleophile. I've tried attacking various carbonyls on the chain but cannot attain the desired product. Any help would be greatly appreciated, thank you.

[kriggy]

What about aldol reaction?

[confusedug45]

It looks like an aldol reaction and the aldehyde part would be the most electrophilic but it doesn't get the right product unless there is an additional step. I think it might be an aldol then rearrangement

[kriggy]

It looks like an aldol reaction and the aldehyde part would be the most electrophilic but it doesn't get the right product unless there is an additional step. I think it might be an aldol then rearrangement

Exaclty. I didnt want to just give you the answer. Try to draw the aldol and figure out the rearrangement I think youre on a good way

[confusedug45]

I got the second step, it's just intramolecular nucleophilic attack from the O, followed by tautomerisation and then an e1cb. Still no luck with first step. I know it involves an aldol but could you give me a hint as to what else? or where the aldol attacks?

[rolnor]

It must be a acetylation-step also? Or does the acetyl migrate?

[confusedug45]

I've figured it out, thank you for the help.

[kriggy]

I've figured it out, thank you for the help.

Can you show us? Maybe someone else in the fufuture might be interested in smiliar kind of problem

[confusedug45]

Yeah sure