[phenooo]

Hi guys, I'm having trouble with this reaction. Basically in the image I attach, I need to get from the first compound to the last compound I drew. I just don't know if my steps will work. I put in a protecting group on the alcohol, then proceeded to put the compound in with mg in ether to form the grignard reagent. Then I added C(CH3)2O to the mixture to get it to react and form the tertiary alcohol. I then removed the protecting group with TBAF and then used PCC to oxidize it. If I understand correctly PCC will oxidize a primary and secondary alcohol but nothing will happen to the tert alcohol. Then I used the gilman reagent to add the ethyl group through conjugate addition. Would this work or am I messing up somewhere?
Thanks for all the help guys!

[mst]

I think it's fine till the last step. I think gilmans reagent isn't compatible to the alcohol.
Your steps are fine but in the wrong order.
First oxidize, use gilman and directly quench with tbdmsCl to get the protected enol ether. Then make grignard reaction and deprotect with tbaf which will yield the product.