Heterodendralenes have received increasing attention as building blocks for multiple cycloaddition reactions, namely diene-transmissive hetero-Diels-Alder (DTHDA) reactions, which lead to the rapid generation of molecular complexity. Therefore, the DTHDA protocol is an efficient and attractive method for stereoselective synthesis of a variety of heterocycles. In this review, DTHDA reactions of four different [3]heterodendralenes are described.