hey guys, found this potent noid, but cant find the full synthesis writeup.
in https://pubs.acs.org/doi/10.1021/jm970126f
they make 11-Hydroxycannabinol-DMH (compund 4b) from 11-hydroxy-∆8-THC diacetate (compund 5b):
But i cant find anything about 11-hydroxy-∆8-THC diacetate (is it a metabolite?) Is there a doable synthesis for this?
in https://pubs.acs.org/doi/10.1021/jm970126f
they make 11-Hydroxycannabinol-DMH (compund 4b) from 11-hydroxy-∆8-THC diacetate (compund 5b):
11-hydroxy-∆8-THC diacetate (5b) ---> 4c
Dehydrogenation of the DMH homolog of
11-hydroxy-∆8-THC diacetate (5b) with sulfur at 240
°C led to the DMH homolog of 11-hydroxycannabinol
diacetate (4c), which was converted to the diol 4b
Dehydrogenation of 5b:
The dehydrogenations were carried out by heating each compound with
sulfur at 238-240 °C, under a nitrogen atmosphere, for ca. 4
h. Mixture was extracted with ether and evaporated.
The residue was chromatographed on a silica gel column using
variable concentrations of ether in petroleum ether as eluent.
Compound 5b gave 4c;
4c ---> 4b (11-Hydroxycannabinol-DMH):
11-Hydroxycannabinol-DMH (4b):
Compound 4c (526mg, 1.13 mmol) in dry ether (10 mL) was added to lithium
aluminum hydride (123 mg) in dry ether (8 mL). The mixture
was boiled under reflux for 2 h. The oil obtained after workup
was chromatographed on a silica gel column (60 g). Elution
with 20% ether in petroleum ether gave, after crystallization
from pentane, compound 4b (340 mg, 78%): mp 128-130 °C;
1H NMR (CDCl3) δ 8.45, 7.255, 7.253, 6.60, 6.40 (s, 5H), 4.75
(s, 2H), 1.65-0.8 (m, 2H). Anal. (C25H 34 O3) C,H
Dehydrogenation of the DMH homolog of
11-hydroxy-∆8-THC diacetate (5b) with sulfur at 240
°C led to the DMH homolog of 11-hydroxycannabinol
diacetate (4c), which was converted to the diol 4b
Dehydrogenation of 5b:
The dehydrogenations were carried out by heating each compound with
sulfur at 238-240 °C, under a nitrogen atmosphere, for ca. 4
h. Mixture was extracted with ether and evaporated.
The residue was chromatographed on a silica gel column using
variable concentrations of ether in petroleum ether as eluent.
Compound 5b gave 4c;
4c ---> 4b (11-Hydroxycannabinol-DMH):
11-Hydroxycannabinol-DMH (4b):
Compound 4c (526mg, 1.13 mmol) in dry ether (10 mL) was added to lithium
aluminum hydride (123 mg) in dry ether (8 mL). The mixture
was boiled under reflux for 2 h. The oil obtained after workup
was chromatographed on a silica gel column (60 g). Elution
with 20% ether in petroleum ether gave, after crystallization
from pentane, compound 4b (340 mg, 78%): mp 128-130 °C;
1H NMR (CDCl3) δ 8.45, 7.255, 7.253, 6.60, 6.40 (s, 5H), 4.75
(s, 2H), 1.65-0.8 (m, 2H). Anal. (C25H 34 O3) C,H
But i cant find anything about 11-hydroxy-∆8-THC diacetate (is it a metabolite?) Is there a doable synthesis for this?