67119-85-1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 67119-82-8 1-(2-Methoxy-4-trimethylsilanyloxy-cyclohex-3-enyl)-ethanone 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 488787-31-1 6-[(1-hydroxy-1-methyl)ethyl]-3-ethoxy-2-cyclohexen-1-one 
• 104841-04-5 2-(2-Methoxy-4-trimethylsilanyloxy-cyclohex-3-enyl)-propan-2-ol 

Downstream Products

• 488787-45-7 (R)-4-[(1-hydroxy-1-methyl)ethyl]-2-cyclohexen-1-one 
• 136954-91-1 (+/-)-11-oxo-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether 
• 123331-92-0 2-((1R,6R)-3-[1,3]Dithian-2-yl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol 
• 52663-85-1 11-oxo-6a,10a-trans-Δ⁹-THC 
• 28623-60-1 (+/-)-11-hydroxy-Δ⁹-tetrahydrocannabinol 
• 80113-04-8 (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol 

Relevant academic research and scientific papers

Cannabidiol derivative as well as preparation method and medical application thereof

The invention relates to a cannabidiol derivative and application thereof in medicine, in particular to a pyrimidine derivative as shown in a general formula (I), or a stereoisomer, a solvate, a metabolite, a prodrug, a pharmaceutically acceptable salt or a co-crystal thereof, and definition of each substituent in the general formula (I) is the same as that in the specification.

Cannabidiol derivative as well as preparation method and medical application thereof

The invention relates to a cannabidiol derivative and application thereof in medicine, in particular to a pyrimidine derivative as shown in a general formula (I), or a stereoisomer, a solvate, a metabolite, a pharmaceutically acceptable salt or a co-crystal thereof, with definition of each substituent in the general formula (I) being the same as that in the specification.

Synthesis of Racemic and Optically Active Δ9-Tetrahydrocannabinol (THC) Metabolites

The preparation of racemic and optically active Δ9-THC metabolites is described from synthon 13.Racemic synthon 13 is prepared in four steps (46percent) from Danishefsky's diene.Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23percent yield).Alternatively, nopinone can be converted to 13 in three steps (50percent yield) via a cyclobutane ring cleavage.The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl Δ9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4 b from 5-(1',1'-dimethylheptyl)resorcinol (6c).

A terpenic synthon for Δ1-cannabinoids

The reversal of the reactivity (i.e., umpolung) of carbonyl compounds when masked as dithioacetals has been shown to be of use for the elaboration of organic molecules. We have applied this principle to the synthesis of metabolites of Δ1--tetrahydrocannabinol (THC, 1) by preparing the novel cis- and trans-terpenes 7 and 8, which contain the dithiane masking group, and condensing them with olivetol under acid catalysis.