6087-61-2

Upstream product

• 3556-79-4 (6aR*,10aR*)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-dibenzopyran-1-ol 
• 114534-53-1 2-[(1R,6R)-3-Methyl-6-(1-methyl-1-trimethylsilanyloxy-ethyl)-cyclohex-3-enyl]-5-pentyl-3-triisopropylsilanyloxy-phenol 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 94450-80-3 1,3-Bis(methoxymethoxy)-5-pentylbenzene 
• 488787-28-6 4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 351187-65-0 2-iodo-4-[(1-methyl-1-triethylsilyloxy)ethyl]-2-cyclohexen-1-one 
• 488787-31-1 6-[(1-hydroxy-1-methyl)ethyl]-3-ethoxy-2-cyclohexen-1-one 
• 488787-32-2 6-[(1-methyl-1-triethylsilyloxy)ethyl]-3-ethoxy-2-cyclohexen-1-one 
• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 500-66-3 Olivetol 
• 114534-51-9 (1S,6S)-6-Acetyl-3-methyl-cyclohex-3-enecarboxylic acid ethyl ester 
• 114534-52-0 (4R,5R)-1-Methyl-4-(1-methyl-1-trimethylsilanyloxy-ethyl)-5-triisopropylsilanyloxyethynyl-cyclohexene 
• 78-79-5 isoprene 

Downstream Products

• 76207-25-5 (6aR,10aR)-6,6,9-Trimethyl-3-pentyl-1-phenoxy-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene 
• 16849-44-8 Δ^9,11-hexahydrocannabinol 

Relevant academic research and scientific papers

High-pressure diels-alder cycloadditions between benzylideneacetones and 1,3-Butadienes: Application to the synthesis of (R,R)-(-)- and (S,S)-(+)-Δ8-tetrahydrocannabinol

High-pressure Diels-Alder reactions of various alkoxy/alkyl-substituted benzylideneacetones with methyl-1,3-butadienes are reported. Activation by high pressure (8-11 kbar) in combination with the mild Lewis acid HfCl 42THF allows these reactions to efficiently and regioselectively produce a series of ortho-substituted cyclohexenyl-benzene cycloadducts, that are useful precursors for the expeditious construction of the privileged 6,6-dimethyltetrahydro-6H-benzo[c]chromene skeleton. Application to the synthesis of Δ8-trans-THC in both enantiomeric pure forms is based on the successful resolution of selected cycloadduct by the SAMP-hydrazone method.

Synthesis of tetrahydrocannabinols based on an indirect 1,4-addition strategy

The synthetic procedure presented for the preparation of the title compounds requires 1,4-addition of bulky cuprates to cyclohexenones and subsequent reaction with electrophiles. However, the enolates generated by BF3·OEt2-assistance suffer from lack of nucleophilicity. To circumvent this problem, we developed an indirect method consisting of the following three steps: (1) iodination of the cyclohexenones at the α position; (2) BF3·OEt2-assisted 1,4-addition of cuprates (Ar2Cu(CN)-Li2, Ar = aryl) followed by quenching the enolates with water; (3) reaction of the α-iodo-β-arylcylohexanones thus formed with EtMgBr to generate magnesium enolates. The enolates thus generated in this way showed a high reactivity toward ClP(O)(OEt)2 to furnish enol phosphates. The aforementioned procedure was also applied to a synthesis of optically active Δ9-tetrahydrocannabinol. In addition, a naphthalene analogue of the latter compound was also synthesized in a similar way.

Hashish: Factors Influencing Double-Bond Stability in Cannabinoids

It is shown that Bucourts methods for estimating torsion strain can be successfully applied to the THC ring system to give a surprisingly good quantitative estimate of the relative stability of various THC double bond isomers (Table II). trans-C1/su