Abstract Two novel cannabinoid model compounds,(3R, 4R)-Δ 1 (6)-tetrahydrocannabinol-5 ″-oic acid (22) and 4 ″(R, S)-methyl-(3R, 4R)-Δ 1 (6)-tetrahydrocannabinol-5 ″-oic acid (23) were synthesized by acid-catalyzed condensation of (+)-trans-p-mentha-2, 8-dien-l-ol (1) with the substituted resorcinols 18 and 19 obtained by a Wittig reaction between 3, 5-bis (benzyloxy) benzaldehyde (7) and methyl 4-bromobutanoate (10) or methyl 4-bromo-2 (R, ...