The following conversion can be performed in a few steps. Show key intermediates and reagents (detailed mechanisms are not required).

So I've been looking at this for a while and I can't seem to figure it out. If someone could please help me by telling what kinds of reactions/reagents I should use in this synthesis. The mechanism is not necesarry to show, since I can do that myself, I just need help with which reaction path to follow.

  • $\begingroup$ It is easier to work backwards. How can you make a C–O bond beta to a carbonyl group? $\endgroup$ – orthocresol May 8 '19 at 22:23
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    $\begingroup$ To my knowledge the starting material doesn't exist as drawn. It exists as its tautomer, alpha-naphthol. $\endgroup$ – user55119 May 8 '19 at 22:53
  • $\begingroup$ Oh, I feel silly for not spotting that now. The original question did indicate that this was the starting material. But of course, it would tautomerise... $\endgroup$ – orthocresol May 8 '19 at 23:30
  • $\begingroup$ So if I use Baeyer Williger to add oxygen next to the ketone, I get a 7 membered ring, but where do I go from there? $\endgroup$ – Simone Maarup Pedersen May 9 '19 at 12:03
  • $\begingroup$ If you react the [7] ring lactone under base hydrolysis conditions the phenoxide generated will attack the unsaturated ester 1,4 to give the free acid of the required product. Then just esterify. The big question is whether 1-naphthol undergoes B-V in this manner and I can find no reference for this. Can anyone else? $\endgroup$ – Waylander May 9 '19 at 20:41

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