The therapeutic effects of molecules produced by the plant species Cannabis sativa have since their discovery captured the interest of scientists and society, and have spurred the development of a multidisciplinary scientific field with contributions from biologists, medical specialists and chemists. Decades after the first isolation of some of the most bioactive tetrahydrocannabinols, current research is mostly dedicated to exploiting the chemical versatility of this relevant compound class with regard to its therapeutic potential. This review will primarily focus on synthetic pathways utilised for the synthesis of tetrahydrocannabinols and derivatives thereof, including chiral pool-based and asymmetric chemo- and biocatalytic approaches.