3410-84-2

Upstream product

• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 58545-48-5 (E)-1,3-dimethoxy-5-(pent-1-en-1-yl)benzene 
• 500-66-3 Olivetol 
• 38228-28-3 1-(1-hydroxypentyl)-3,5-dimethoxybenzene 
• 7311-34-4 3,5-dimethoxybenzaldehdye 

Downstream Products

• 59131-20-3 (E)-3-(2,6-dimethoxy-4-pentylphenyl)acrylic acid 
• 81482-15-7 ((2,6-dimethoxy-4-pentylphenyl)methylidene)malonitrile 
• 162330-77-0 2-hydroxy-6-methoxy-4-pentylbenzaldehyde 
• 3411-09-4 2.6-Dimethoxy-4-pentyl-benzalaceton 
• 20675-51-8 cannabichromene 
• 57412-30-3 5-methoxy-2-methyl-2-(4-methyl-3-pentenyl)-7-pentyl-2H-chromene 
• 81482-23-7 2-(2,2-dicyano-5-oxocyclohexyl)-1,3-dimethoxy-5-pentylbenzene 
• 81482-22-6 2-(2,2-dicyano-5-oxo-3-cyclohexenyl)-1,3-dimethoxy-5-pentylbenzene 
• 81482-26-0 2(2-cyano-5-ethylenedioxycyclohexyl)-1,3-dimethoxy-5-pentylbenzene 
• 81482-27-1 2(2-ethyloxy-5-ethylenedioxycyclohexyl)-1,3-dimethoxy-5-pentylbenzene 
• 81482-28-2 2(2(1-hydroxyisopropyl)-5-ethylenedioxycyclohexyl)-1,3-dimethoxy-5-pentylbenzene 
• 81482-21-5 2-(2,2-dicyano-3-methoxy-5-oxocyclohexyl)-1,3-dimethoxy-5-pentylbenzene 
• 81482-24-8 2-(2,2-dicyano-5-ethylenedioxycyclohexyl)-1,3-dimethoxy-5-pentylbenzene 
• 81482-20-4 2-(2,2-dicyano-3-methoxy-5-(trimethylsiloxy)-4-cyclohexenyl)-1,3-dimethoxy-5-pentylbenzene 

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.

7-alkyl-3-benzylcoumarins: A versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists

A series of 7-alkyl-3-benzylcoumarins was designed, synthesized, and tested at cannabinoid CB1 and CB2 receptors in radioligand binding and cAMP accumulation studies. 7-Alkyl-3-benzylcoumarins were found to constitute a versatile scaffold for obtaining potent CB receptor ligands with high potency at either CB1 or CB2 and a broad spectrum of efficacies. Fine-tuning of compound properties was achieved by small modifications of the substitution pattern. The most potent compounds of the present series include 5-methoxy-3-(2-methylbenzyl)-7-pentyl-2H-chromen-2-one (19a, PSB-SB-1201), a selective CB1antagonist (Ki CB 1 0.022 μM), 5-methoxy-3-(2-methoxybenzyl)-7-pentyl-2H-chromen-2- one (21a, PSB-SB-1202), a dual CB1/CB2agonist (CB 1Ki 0.032 μM, EC50 0.056 μM; CB 2Ki 0.049 μM, EC50 0.014 μM), 5-hydroxy-3-(2-hydroxybenzyl)-7-(2-methyloct-2-yl)-2H-chromen-2-one (25b, PSB-SB-1203), a dual CB1/CB2 ligand that blocks CB 1 but activates CB2 receptors (CB1Ki 0.244 μM; CB2Ki 0.210 μM, EC50 0.054 μM), and 7-(1-butylcyclopentyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2- one (27b, PSB-SB-1204), a selective CB2 receptor agonist (CB 1Ki 1.59 μM; CB2Ki 0.068 μM, EC50 0.048 μM).

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 (-)-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

The Diels-Alder approach towards cannabinoids

Starting from the efficient synthesis of benzopyrans by base-catalyzed condensation reactions between substituted 2-hydroxybenzaldehydes and α,β-unsaturated aldehydes, thermal, Lewis acid catalyzed and enantioselective organo-promoted Diels-Alder reactions towards the tricyclic cannabinoid system are presented. The procedures are exemplified by the synthesis of a pentacycle and various tricycles respectively, in up to 95% enantiomeric excess and provide a versatile entry to this group of natural products with tetrahydrocannabinol (THC) being the most prominent one. Most published strategies are based on the formation of the tricyclic system by condensation between readily available phenols and monoterpenes, whereas we present a novel approach to cannabinoid derivatives based on a modular synthesis. Georg Thieme Verlag Stuttgart.