[puppy8800]

My classmate shared this synthesis question with me.
Organic reagents given are merely the three substances on the top, and the target molecule is the one on the bottom.
I've noticed that the second reagent is placed at the rightmost situation, while the third reagent seems ambiguous in TM.
I have completely no idea of how to make up the conjugated ring...
Could anyone give me some help?
Sorry for my poor English...

Thanks before.

[Rico]

Hey puppy8800

A possible synthesis could be as follows (see jpeg attached):

Cyclohexanon is treated with base and the enolate then undergoes a conjugate substitution with the first reagent. The product isomerizes under the basic conditions and gives after acidic workup, A. A is treated with the second reagent under acidic conditions and gives after addition, elimination (E1cB) and cyclization the product B. B is hydrolysed, decarboxylated and the tautomerized to C. C is reesterified and finally alkylated to the product.

I hope this will be of help to you.

Rico

[puppy8800]

Thanks very much, Rico.
I've got it.

[Mitch]

Is that the right answer more or less?:

[Rico]

Is that the right answer more or less?:

Actually i don't know, it was merely a suggetion at the top of my theoretical mind 
I just made a quick search in the litterature and i wasn't able to find anything. Maybe it will work i don't know, it has to be tried out in the lab!
If somebody has another more plausible suggestion i would be happy to see it!


Rico

[Fry]

would this work?

Turn that acetal into acetaldehyde and condense it with the cyclohexanone to form alpha-ethyl cyclohexanone (after hydrogenation). From there, irradiate it with UV light and carry out a norrish type II reaction to abstract the gamma hydrogen.. hopefully the diradical intermediate will cyclize to form the four membered cyclobutane ring with a tertiary alcohol. Dehydrate this to form the cyclobutene and carry out a ring opening to form the diene.

Once youve got the diene its just a simple diels alder reaction with that diester dienophile youve got up there.. ill draw it out

[Fry]

Sorry if anything is wrong or off.. Im kinda new at this stuff 

I dont know how to go about dehydrating that ring effectively...

Also, that first reaction may be kinda iffy (the acetaldehyde will probably want to self condensate, no?) Is there a way to do it successfully?

constructive criticism, please