The Diels-Alder Approach towards Cannabinoid Derivatives and Formal Synthesis of Tetrahydrocannabinol (THC)

Thomas Hurrle, Franziska Gläser, Manuel C. Bröhmer, Martin Nieger, Stefan Bräse
2021
Based on the Diels-Alder reaction of vinylchromenes with electron-poor dienophiles, we developed a strategy for the synthesis of tetrahydrocannabinol derivatives. Substituted vinyl chromenes could be converted with several dienophiles to successfully isolate several complex molecules. These molecules already contain the cannabinoid-like base structure and further processing of one such derivative led to a precursor of Δ$^{9}$-tetrahydrocannabinol. The most challenging step towards this
more » ... was an epoxidation step that was ultimately achieved via dimethyl dioxirane.
doi:10.5445/ir/1000133846 fatcat:vxwgmd6icraufciuizcqxcosv4