1310045-86-3

Upstream product

• 1310045-82-9 (2''S)-N-{1-[(1S,2S)-2-(2',6'-dimethoxy-4'-pentylphenyl)-4-methylcyclohex-3-en-1-yl]ethylidene}-2''-(methoxymethyl)-pyrrolidin-1''-amine 
• 3410-84-2 2,6-dimethoxy-4-pentylbenzaldehyde 
• 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 

Downstream Products

• 1310045-89-6 2-((1S,2S)-2-(2'-hydroxy-6'-methoxy-4'-pentylphenyl)-4-methylcyclohex-3-enyl)propan-2-ol 

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.