Synthesis of optically active (−)-11-Nor-Δ9-tetrahydrocannabinol-9- carboxylic acid

Baek, Seung‐Hwa; Szirmai, Maria; Halldin, Magnus M.

doi:10.1016/0091-3057(91)90351-2

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A urinary metabolite of Δ1-tetrahydrocannabinol. The first synthesis of 4′′-hydroxy-Δ1-tetrahydrocannabinol-7-oic acid labelled with deuterium

Szirmai

Odqvist

Halldin

1996

J Label Compd Radiopharm

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SUMMARYThe first synthesis of 4"-hydroxy-A1-THC-7-oic acid, one of the three major metabolites of AI-THC identified in human urine is discussed. Methyl 4-(3,5-dihydroxyphenyl)butanoate (8) was prepared from 3,5-dihydmxybenzoic acid in an overall yield of 15%. 8 was condensed with a terpene synthon (9) under acidic conditions followed by hydrolysis and conversion of the 4"-carboxylic acid function to the corresponding methyl ketone using methyllithium. Reduction with NaBQ afforded the secondary alcohol in the side-chain. Acetylation and removal of the 13-dithiane masking group gave the aldehyde in C-7-position which was further oxidized using N a C Q followed by deacetylation to give the desired metabolite 14. The same procedure may be used for the synthesis of unlabelled 4"-hydroxy-A*-THC-7-oic acid.

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