930598-05-3

Upstream product

• 1310045-80-7 (2''S)-N-{(1E)-1-[(1R,2R)-2-(2',6'-dimethoxy-4'-pentylphenyl)-4-methylcyclohex-3-en-1-yl]ethylidene}-2''-(methoxymethyl)pyrrolidin-1''-amine 
• 1310045-84-1 1-(2',6'-dimethoxy-5-methyl-4'-pentyl-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)ethanone 
• 75-16-1 methylmagnesium bromide 
• 7663-54-9 2',6'-dimethoxy-1'-((E)-3-methylbuta-1,3-dienyl)-4'-pentylbenzene 
• 3411-09-4 (E)-4-(2,6-dimethoxy-4-pentylphenyl)but-3-en-2-one 
• 930598-01-9 2-[1-(2,6-dimethoxy-4-pentylphenyl)allyl]-5-methyl-5-hexenoic acid methyl ester 
• 930597-96-9 dimethyl [1-(2,6-dimethoxy-4-pentylphenyl)allyl]malonate 
• 930598-00-8 3-(2,6-dimethoxy-4-pentyl-phenyl)-pent-4-enoic acid methyl ester 
• 930598-04-2 2-(2,6-dimethoxy-4-pentylphenyl)-4-methyl-cyclohex-3-enecarboxylic acid methyl ester 

Downstream Products

• 488787-51-5 (3R,4R)-3-[(2-hydroxy-6-methoxy-4-pentyl)phenyl]-1-methyl-4-[(1-methyl-1-triethylsilyloxy)ethyl]-1-cyclohexene 
• 1972-08-3 dronabinol 
• 36403-68-6 D1,2-Tetrahydrocannabinol methyl ether 

Relevant academic research and scientific papers

High-pressure access to the Δ9-cis - And Δ9-trans-tetrahydrocannabinols family

Diels-Alder reactions of a range of 1-(alkoxy/alkyl-substituted phenyl)buta-1,3-dienes with methyl vinyl ketone and methyl acrylate carried out in ethanol as the reaction medium under 9 kbar pressure were investigated. The use of high pressure as the activating method of the Diels-Alder reactions allows the efficient and endodiastereoselective generation of a series of cis-cyclohexenyl-benzene cycloadducts, which are selectively converted into their trans-epimers. The cis-cyclohexenyl-benzenes and trans-cyclohexenyl- benzenes produced are useful precursors for accessing substituted privileged cis-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene and trans-6a,7,8,10a-tetrahydro- 6H-benzo[c]chromene skeletons. The total syntheses of Δ9-cis- tetrahydrocannabinol (THC) and Δ9-trans-THC, through the use of selected Diels-Alder adducts, are described. Finally, a route for obtaining Δ9-trans-THC in both enantiomeric pure forms based on the (S)-(-)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP)-hydrazone method is also reported.

Synthesis of (-)-Δ9-trans-tetrahydrocannabinol: Stereocontrol via mo-catalyzed asymmetric allylic alkylation reaction

(Chemical Equation Presented) Δ9-THC is synthesized in enantiomericaly pure form, where all of the stereochemistry is derived from the molybdenum-catalyzed asymmetric alkylation reaction of the extremely sterically congested bis-ortho-substitut