[Isaac]

How would you synthesize 3,5 dimethyl-2-cyclohexene-1-one using 2-butanone and 3-buten-2-one as the starting material?

I did try using Mander's reagent and have also condsidered Micheal addition, but so far I'm still stuck. Any help would be appreciated.

[movies]

There is a name reaction that can do this is one step (kind of).

You're on the right track, I think.  What would have to happen subsequent to a Michael addition?

[Isaac]

ok, this is what I'm doing, I'm adding LDA to 2-butanone, and then adding Mander's reagent to it. Then I'm adding LDA to 3-buten-2-one, and adding this to methyl 3-oxopentanoate ( which is made by 2-butanone and the mander's reagent). This should then cyclized to 3,5 dimethyl-2-cyclohexene-1-one. This does not seem to work, and I'm running out of ideas to tackle this.

I did not know that you could do this reaction in a single step. How would I go about doing it in a single step? ( I need some sort of stepping stone). Waiting for replies.    

[movies]

Oops, I think I made a mistake.  It's not supposed to be 3,6-dimethyl?  It just seems too easy for this one name reaction.  The 3,5 isomer is going to be a lot more difficult.  I can't imagine there will be that much use of Mander's reagent in this problem.