The supported ruthenium-catalyzed oxidation of the 1,2-dihaloalkene moiety in tetrahalo-norbornyl derivatives possessing acid labile functionalities to afford the corresponding α-diketones is demonstrated. The protocol was successfully applied in the synthesis of a cyclopenta-annulated δ-lactone derived from D-mannitol. & © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.