I have an assignment in my organic class (First semester of organic for chemistry majors) to show how to perform the following synthesis.
We can only use reactions that we have covered in class this semester which include: alkene additions (hydroboration, oxymercuration, etc.), reactions of alcohols (oxidation, converting to tosylates/mesylates, reduction), epoxide formation and breaking reactions, nucleophilic substitution and elimination, metathesis reaction, Grignard reaction, cleavage of glycols. We are graded on using the most efficient method, and get bonus points if we include another method.
I started and am stuck on how to get the starting material to a ring. I'll post what I have so far and I would appreciate any advice on where to go from here.
Step 1 (working backwards):
Either step would work, I assume the peroxyacid one would be more efficient though.
Step 2: (t-butoxide is supposed to be over the reaction arrow)
This is where I am stuck, I'm not sure how to get the starting material into a cyclobutane/ene ring. I have one possible method figured out, but I'm not sure how well it would work.
Any advice/help would be much appreciated. Thanks in advance.