The synthesis of some 11-substituted tetrahydrocannabinol metabolites

Article abstract of DOI:10.1139/v82-403

9-Bromo-11-oxo-hexahydrocannabinol (5) was prepared from the ketocannabinoid 3b via the epoxysulfone 4.The dehydrobromination of the bromoaldehyde 5 could be controlled to give either the thermodinamically more stable Δ⁸-aldehyde 2c, or the Δ⁹-aldehyde 1c by an intramolecularly assisted elimination.Reduction of the unsaturated aldehydes gave the allylic alcohol metabolites 2a and 1a, respectively.