Haschisch‐Inhaltsstoffe. 7. Mitteilung. Synthese von (−)‐11‐Hydroxy‐Δ⁸‐6a, 10a‐trans‐Tetrahydrocannabinol

Abstract

When (−)‐Δ8‐6a, 10a‐trans‐THC (THC = Tetrahydrocannabinol), in the form of its diacetate, was irradiated in the presence of oxygen and a sensitizer, followed by reduction with NaBH4, three allylic alcohols were formed: (−)‐8α‐and (−)‐8β‐hydroxy‐Δ9,11‐THC (proportion 3:1) and (−)‐9α‐hydroxy‐Δ7,8‐THC. Acetylation of the epimeric 8‐hydroxy‐compounds with Ac2O/pyridine gave the corresponding diacetates. When (−)‐Δ8‐6a, 10a‐trans‐THC, in the form of its tetrahydropyranyl derivative, was heated with m‐chloroperbenzoic acid, the two epimeric 8,9‐epoxides were formed in equal amounts. These compounds, on treatment with butyllithium, afforded (−)‐8α‐ and (−)‐8β‐hydroxy‐Δ9,11‐ 6a, 10a‐trans‐THC‐tetrahydropyranylether. After removing the protecting group and treatment with Ac2O/pyridine the same diacetates, as formed by photooxygenation of (−)‐Δ8‐THC‐acetate, were obtained as a 1:1‐mixture. On heating these epimeric diacetates to 290° they underwent allylic rearrangement to (−)‐11‐acetoxy‐Δ8‐THC‐acetate. From this (−)‐11‐hydroxy‐Δ8‐6a, 10a‐trans‐THC was obtained by treatment with LiAlH4.

Conversion of cannabidiol to Δ9-tetrahydrocannabinol and related cannabinoids in artificial gastric juice, and their pharmacological effects in mice

“…8-Hydroxy-iso-HHC (8-OH-iso-HHC) and 9α-hydroxy-HHC (9α-OH-HHC) were prepared by the methods of Gaoni and Mechoulam [7] and Petrzilka et al [11], respectively. The purities of these cannabinoids were checked to be more than 98% by gas chromatography (GC).…”

Plasma and Brain Levels of Δ6‐THC and Seven Monooxygenated Metabolites Correlated to the Cataleptic Effect in the Mouse

“…The synthesis of (-)-1"-'H-3,4-rrans-A6-THC (A'=A* in the benzopyran numbering system) with a specific activity of 25.3 mCi/mmol has been described earlier . The synthesis of EHHCacetate from A'-THC has been reported elsewhere (Petrzilka & Demuth 1974). This acetate was hydrolyzed in 4 M sodium hydr0xide:methanol ( 1 : l ) at room temperature for 5min to yield the EHHC.…”