The synthesis of caged bis-hemiacetals and their facile conversion to symmetric bis-α-halo-γ-lactones was discussed. A direct and convenient access to the α-monobromo-bis-γ-lactone was achieved using the base-catalyzed deprotection of the dibromo diketo diacetate in good yield. An expedient synthesis of the cis, syn, cis-bis-γ-lactone in excellent yield was also established.