Helvetica Chimica Acta p. 2508 - 2514 (1980)
Update date:2022-08-17
Topics:
Franke, Ingo
Binder, Michael
Two novel cannabinoid model compounds, (3R,4R)-Δ1(6)-tetrahydrocannabinol-5"-oic acid (22) and 4"(R,S)-methyl-(3R,4R)-Δ1(6)-tetrahydrocannabinol-5"-oic acid (23) were synthesized by acid-catalyzed condensation of (+)-trans-p-mentha-2,8-dien-1-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,S)-methylbutanoate (11) resp. with subsequent hydrogenation.The resulting methyl esters 20 and 21 were hydrolyzed to give acids 22 and 23.
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