Oligomeric sesquiterpenoids, biogenetically assembled from two or three monomeric sesquiterpenoid units via diverse pathways, represent a unique class of natural products. The synthetic studies inspired by their biogenesis have offered significant impetus for the efficient construction of these architecturally complex frameworks. Here we provide an overview for the biomimetic syntheses of these dimeric and trimeric molecules based on the different strategies of bond formation, including Diels-Alder reaction, hetero-Diels-Alder reaction, [2 + 2] cycloaddition, and C-C bond coupling.