[sharbeldam]

I have this dicarbonyl, i tried everything to get to that product, nothing works, i think the obvious first move is aldol, after that I can do oxidation, haloform reaction... and many other options, but nothing works, how can i get two methyls?? any hints at all?

[sharbeldam]

Edit : another thought, please tell me if im right.
1) aldol
2) haloform
3) oxidation of the alcohol so it can become ketone
4) decarboxylation
5) alpha alkylation (+CH3)
6) reducing my ketone back to alcohol
7)PBr3 --> Mg --> Alcohol becomes MgBr
CO2 so i get carboxylic acid
9) I reduce the CA and eliminate the alcohol + H2/pd

[rolnor]

What about the carbon alpha to the aldehyde attacking the kenone carbonyl first?

[sharbeldam]

I dont know why but that made me laugh, i did 9 steps for nothing, thanks rolnor !!

[Meter]

I dont know why but that made me laugh, i did 9 steps for nothing, thanks rolnor !!

Aldehyde alpha carbons are more acidic than ketone alpha carbons. Something to keep in mind for these types of problems.

[rolnor]

No problem!