Synthesis of Δ1 and Δ1(6) tetrahydrocannabinol metabolites
✍ Scribed by Z. Ben-Zvi; R. Mechoulam; S.H. Burstein
- Book ID
- 108383178
- Publisher
- Elsevier Science
- Year
- 1970
- Tongue
- French
- Weight
- 137 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
It is well documented 2,3,4,5 that the primary reaction in the metabolism of A'-and Al(e) -THCs\* (la and 2a) is oxidation to the 7-hydroxy derivatives J& and &.
Condensatzon of I,&bzs(trunethylszloxyl-I-methoxybutadiene wzth the aced chloride ;z gave methyl olivetolate (;?I. Condensatzon of 22 wzth (+I-p-mentha-2,8-dzenl-01 gave methyl Al-tetrahydrocannabinolate (14) zn 55% zsolated yzeld. Alkalzne hydrolyses of lg gave Al-tetrahydrocannabznol-72, Al-THCI.
The 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) unde