This paper describes Compiler-Directed Content-Aware Prefetching (CDCAP), an integrated compiler and hardware approach for prefetching dynamic data structures. The approach utilizes compiler-inserted prefetch instructions to convey information about a dynamic data structure to a prefetching engine. The technique eliminates the need to transform the data structure without the use of excessive prefetches and does not require prior knowledge of data traversals. The approach also eliminates the need for large hardware structures and reduces unnecessary prefetches. For pointer intensive programs, the CDCAP approach reduces memory stall time by up to 40% and out performs previously proposed prefetching techniques.