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- Title
Synthesis of cannabinoid model compounds. Part 2: (3 R, 4 R)-Δ<sup>1(6)</sup>-Tetrahydrocannabinol-5″-oic acid and 4″( R, S)-Methyl-(3 R, 4 R)-Δ<sup>1(6)</sup>-tetrahydrocannabinol-5″-oic Acid.
- Authors
Franke, Ingo; Binder, Michael
- Abstract
Two novel cannabinoid model compounds, (3 R, 4 R)-Δ1(6)-tetrahydrocannabinol-5″-oic acid (22) and 4″( R, S)-methyl-(3 R, 4 R)-Δ1(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.
- Publication
Helvetica Chimica Acta, 1980, Vol 63, Issue 8, p2508
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19800630845