Would this work? Step 1 is Michael addition using NaH. Use mild enough conditions that it stops at only the Michael, and does not do a Robinson. Step 2 is to add more NaH to form the next most stable position to have an enolate, creating a dienolate. Step 3 is to add 1 equivalent Br2, or another electrophilic bromine source, to react selectively at the more basic of the two enolates. Step 4 is for the structure to hopefully cyclize naturally via Sn2 at the enolate oxygen. Using sodium as a spectator ion should help in reacting more selectively at oxygen. Step 4 is a Wittig that should be selective for the desired ketone because the other ketone is a vinylogous ester and should be much less reactive.
Ultimately, this is really just two steps, with some waiting in between. Add 1 mol NaH, let it do the Michael. Add another mol NaH to make the next enolate. Add 1 mol Br2, let it cyclize. Then work-up. Then do the Wittig.
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