Hashish (1): Ceric ammonium nitrate oxidation of Δ6a, 1 0 a-tetrahydrocannabinols (THC's)

A procedure is described for the conversion of acetates of Δ^{6a, 1 0 a}-THC's ( 2 and 4a ) to their corresponding 7-oxo-derivatives ( 3a , b , d and 4b ) by oxidation with ceric ammonium nitrate. The differences between the nmr spectra of these 7-oxo-derivatives and the 10-oxo-THC (1) are discussed. The 7-oxo-derivatives show THC-like activity in mice albeit less than their corresponding THC's.