3411-09-4

Usage

InChI:InChI=1/C17H24O3/c1-5-6-7-8-14-11-16(19-3)15(10-9-13(2)18)17(12-14)20-4/h9-12H,5-8H2,1-4H3/b10-9+

Upstream product

• 3410-84-2 2,6-dimethoxy-4-pentylbenzaldehyde 
• 67-64-1 acetone 
• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 500-66-3 Olivetol 

Downstream Products

• 13956-29-1 CBD 
• 930597-95-8 methyl (1R,2R)-2',6'-dimethoxy-5-methyl-4'-pentyl-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-carboxylate 
• 1972-08-3 dronabinol 
• 1242-67-7 O-2797 
• 7663-54-9 2',6'-dimethoxy-1'-((E)-3-methylbuta-1,3-dienyl)-4'-pentylbenzene 
• 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 (+/-)-cis-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 1310045-89-6 2-((1S,2S)-2-(2'-hydroxy-6'-methoxy-4'-pentylphenyl)-4-methylcyclohex-3-enyl)propan-2-ol 
• 1310045-86-3 1-((1S,2S)-2-(2',6'-dimethoxy-4'-pentylphenyl)-4-methylcyclohex-3-enyl)ethanone 
• 1310045-84-1 1-(2',6'-dimethoxy-5-methyl-4'-pentyl-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)ethanone 
• 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 

Relevant academic research and scientific papers

SYNTHESIS OF CANNABINOIDS

Provided are synthesis processes and intermediates for preparing cannabinoids and analogs.

Enantioselective Total Synthesis of Cannabinoids - A Route for Analogue Development

A practical synthetic approach to Δ9-tetrahydrocannabinol (1) and cannabidiol (2) that provides scalable access to these natural products and should enable the generation of novel synthetic analogues is reported.

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.

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.