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A high-yielding route to substituted and functionalized dimethanoanthracenes by the Pd-catalyzed deoxyenation of the corresponding hydroquinone precursors is described. Attempts were made to deoxygenate the 9,10-dimesylate, ditosylate, and ditriflate derivatives of anti-dimethanoanthracene la, and it was found that under the studied conditions only the ditriflate 8a gave the corresponding deoxygenated aromatic scaffold. Optimization of the reaction conditions identified the Pd(OAc)2/dppf tandem as a suitable catalytic system for this transformation. The presented strategy was further extended to a novel and efficient synthetic route to methanoanthracenes employing a one-pot Pd-catalyzed deoxygenation/hydrogenation sequence. [ABSTRACT FROM AUTHOR]