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Stuck on a (condensation?) mechanism...

zyu2ranger
in Organic Chemistry

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Hello. I am struggling with a problem. I have attached it. I cannot rationalize a reasonable mechanism for the transformation of the reactant to the production shown. The initial problem is given at the top of the image. Thank you for any assistance.

I have tried to protonate the -OH group and then have an enol kick out the water to form a carbocation; I've tried to make the enol at the top of the right ring make a 1,3-dicarbonyl and close the ring on the carbon adjacent to the initial OH group... none of these are working. Please assist! Thank you in advance.

Screen Shot 2020-08-17 at 8.59.23 AM.png

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