Stereoselective synthesis of the epimeric Δ7-tetrahydrocannabinols

Abstract Both C9 epimers of Δ 7 -THC (3 and 4) have been synthesized from Δ 8 -THC methyl ether (12). Hydroboration of 12 gave a mixture of stereoisomeric 8-hydroxyhexahydrocannabinols. The 8α-ol was converted into the 9β-methyl epimer ( 4 ) of Δ 7 -THC, while the 8β-ol was converted into 3 . Molecular modeling indicated that 4 should have significant cannabinoid activity, while 3 was predicted to be weakly active. These predictions were borne out by both in vitro and in vivo pharmacology.