23367-60-4

Upstream product

• 127787-60-4 N-[2-Hydroxy-2-(4-methoxy-phenyl)-ethyl]-3,4-dimethoxy-N-methyl-benzamide 
• 110841-25-3 3-Hydroxy-6,7-dimethoxy-4-(4-methoxy-phenyl)-2-methyl-3,4-dihydro-2H-isoquinolin-1-one 
• 50-00-0 formaldehyd 
• 36679-08-0 2-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanamine 
• 16620-96-5 2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 33061-24-4 1-(3,4-dimethoxyphenyl)-2-(dimethylamino)ethanone 
• 2970-95-8 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol 
• 1616788-82-9 [2-(3, 4-dimethoxyphenyl)-2-phenoxyethyl]dimethylamine 
• 1616788-83-0 [2-(3, 4-dimethoxyphenyl)-2-phenoxyethyl]methylcarbamic acid ethyl ester 
• 90-05-1 2-methoxy-phenol 
• 186581-53-3 diazomethane 
• 23367-61-5 (4S)-4-(4-hydroxyphenyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 23349-32-8 O,O-Dimethylcherylline 

Relevant academic research and scientific papers

Lewis Acid-Promoted Regio- and Diastereoselective Cross-Coupling of Aryl-Substituted 1,2-Diols and Boronic Acids

A Lewis acid-promoted highly regio- and diastereoselective C(sp3)-C(sp2) cross-coupling reaction between unprotected aryl-substituted 1,2-diols and styryl-, aryl-, heteroaryl-, and polyarylboronic acids has been developed in a one-pot procedure. The regioselective opening of aryl-substituted cyclic boronic esters promoted by a Lewis acid followed by subsequent intramolecular 1,4-transfer of the carbon ligand from boron to a resonance-stabilized benzylic carbenium ion minimizing the allylic 1,3-strain in a stereoselective fashion led to the corresponding α-substituted syn-phenylethyl alcohols. The synthetic utility of the method was illustrated by a short and efficient enantioselective synthesis of cherylline diethyl ether (-)-16.

New synthesis of (±)-cherylline and mono- and dimethyl ethers

The synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines is achieved via the ether rearrangement methodology. Subsequent reactions yielded cherylline and ether derivatives of amaryllidaceac alkaloids. Copyright

Nucleophilic addition of β-amino carbanions to arynes: One-pot synthesis of 4-aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines

A novel approach for the direct C-4 arylation of N-methyl-1,2,3,4- tetrahydroisoquinolines by nucleophilic addition of β-aminocarbanions to benzynes is described which provides a one-pot procedure for synthesis of the title compounds.

Efficient syntheses of (±)-cherylline and latifine dimethyl ether

A concise route for the syntheses of (±)-cherylline and latifine dimethyl ether is reported. The key steps involved are Michael addition of veratrole with p-methoxy nitrostyrene (for cherylline), anisole with 2,3-dimethoxy nitrostyrene (for latifine), and reduction of nitro intermediate, followed by Pictet-Spengler cyclization. Copyright

An efficient synthesis of (+/-) cherylline dimethyl ether

A concise route for the synthesis of (+/-) cherylline dimethyl ether is reported. The key steps involved are Grignard reaction, conversion of alcohol to nitrile using (N-(p-toluene sulfonyl)imidazole and sodium cyanide), reduction of the nitrile intermedi

A short synthesis of (±)-cherylline dimethyl ether

A synthesis of (±)-cherylline dimethyl ether is reported. The key steps involved are Michael-type addition, radical azidonation of an aldehyde, Curtius rearrangement, and reduction of an isocyanate intermediate followed by Pictet-Spengler cyclization.

Direct syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines via hydroamination of enol carbamates

An efficient and simple procedure for the syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines has been developed. The approach uses easily available starting materials and requires just three steps. The hydroamination of an enol carbamate is the key step. This general and direct method has been applied to the total synthesis of the natural alkaloid cherylline and to biologically active 3-benzoazepines as well.

Synthesis of 4-aryltetrahydroisoquinolines: Application to the synthesis of cherylline

A concise route for the synthesis of 4-aryltetrahydroisoquinolines was developed using the addition of Grignard reagents to nitrostyrene derivatives as the key step. The application to the synthesis of cherylline was described.

Base-induced cyclization of trimethoxy-o-aroyldiphenylphosphoryl methylbenzamide: A formal synthesis of (±)Cherylline and (±)Cherylline dimethylether

The trimethoxy-o-aroyldiphenylphosphorylmethylbenzamide 9 can be cyclized by treatment with KHMDS; the procedure has been employed to synthesize (±)Cherylline 1 and its dimethylether 2.

A convenient synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-4-ols by a novel intramolecular Barbier reaction and by an insertion reaction: Reaction scope and limitations

4-Substituted 1,2,3,4-tetrahydroisoquinolin-4-ols were prepared from N-(2-iodobenzyl)phenacylamines by an intramolecular Barbier reaction with butyllithium and by an insertion reaction with zerovalent nickel. The scope and limitations of these reactions were discussed.