Okay, here are the intermediates. You can see the Bredt's rule intermediate 5. Obviously, I don't know whether the reaction prefers to go through 4 or 9. I concede that thermodynamically, enolization of 3 would be easier than 9. Someone would have to look up whether a retro Claisen of 4 is an easy reaction or not. A carboethoxy bicyclooctan-8-one, or heptanone are probably known and whether is will undergo a retro Claisen should therefore also be known. Without making a model, I don't know if the cleavage to give the enolate would be aligned stereoelectronically. If the reaction went through intermediate 9, the stereoelectronic factors would be easy, but the thermodynamics of enolization would be more difficult, especially if the hydrolysis of the ester occurred simultaneously (by consuming base and forming the carboxylate).
This looks like a reaction I would try on paper, but not in the lab.