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Synthesis of cannabinoid model compounds. Part 2: (3R, 4R)-Δ1(6)-Tetrahydrocannabinol-5″-oic acid and 4″(R, S)-Methyl-(3R, 4R)-Δ1(6)-tetrahydrocannabinol-5″-oic Acid

✍ Scribed by Ingo Franke; Michael Binder

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
410 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Two novel cannabinoid model compounds, (3__R__, 4__R__)‐Δ^1(6)^‐tetrahydrocannabinol‐5″‐oic acid (22) and 4″(R, S)‐methyl‐(3__R__, 4__R__)‐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, 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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