28623-60-1

Upstream product

• 72402-26-7 Acetic acid (6aR,10aR)-9-acetoxymethyl-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl ester 
• 52663-85-1 11-oxo-6a,10a-trans-Δ⁹-THC 
• 67119-86-2 (4R)-1-(1,3-dithianyl)-4-(2-(2-hydroxypropanyl))-2-cyclohexen-1-ol 
• 500-66-3 Olivetol 
• 61597-37-3 4-(1-hydroxy-1-methylethyl)-1-methoxy-1,4-cyclohexadiene 
• 6616-69-9 11-nor-9-keto-6a,10a-cis-HHC 
• 6616-69-9 dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 
• 83889-49-0 9-β-bromo-11-oxo-6a,10a-trans-HHC 
• 67119-85-1 (+/-)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enone 
• 5503-12-8 L-perillaldehyde 
• 89002-23-3 (R)-(+)-4-(2-propenyl)-2-cyclohexen-1-one 
• 123331-88-4 (R)-4-(2-Methyl-oxiranyl)-cyclohex-2-enone 
• 123331-86-2 tert-Butyl-[(R)-4-isopropenyl-cyclohex-2-en-(E)-ylidenemethoxy]-dimethyl-silane 
• 72390-08-0 Acetic acid (6aR,10aR)-6,6-dimethyl-9-methylsulfanylmethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl ester 

Relevant academic research and scientific papers

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).

The synthesis of some 11-substituted tetrahydrocannabinol metabolites

9-Bromo-11-oxo-hexahydrocannabinol (5) was prepared from the ketocannabinoid 3b via the epoxysulfone 4.The dehydrobromination of the bromoaldehyde 5 could be controlled to give either the thermodinamically more stable Δ8-aldehyde 2c, or the Δ9-aldehyde 1c by an intramolecularly assisted elimination.Reduction of the unsaturated aldehydes gave the allylic alcohol metabolites 2a and 1a, respectively.

Synthesis of (±)-11-hydroxy-Δ9-6a,10a-trans-tetrahydrocannabinol and other 11-substituted Δ9-tetrahydrocannabinoids

11-Substituted Δ9-tetrahydorcannabinoids, including the racemate of the biologically important 11-hydroxy-Δ9-6a,10a-trans-tetrahydrocannabinol and the corresponding 11-mercapto analogue, are synthesized via condensation of olivetol with the terpenoid synthon 3 prepared from 6-methylhept-5-en-2-one.