A simple and efficient route for the synthesis of cyclic polymer systems is presented. Linear furan protected alpha-maleimide-omega-cyclopentadienyl functionalized precursors (poly(methyl methacrylate) and poly(tert-butyl acrylate)) were synthesized via atom transfer radical polymerization (ATRP) and subsequent substitution of the bromine end-group with cyclopentadiene. Upon heating at high dilution, deprotection of the dieneo-phile occurs followed by an intramolecular Diels-Alder reaction yielding a high purity cyclic product.