51745-28-9

Upstream product

• 109985-76-4 (+)-(1S,R_S)-N-methyl-3,4-dihydro-6,7-dimethoxy-1-<(p-tolylsulfinyl)methyl>isoquinoline 
• 139750-88-2 (1S,S_R)-N-methyl-6,7-dimethoxy-1-(o-nitrophenylsulfinylmethyl)-1,2,3,4-tetrahydroisoquinoline 
• 138977-23-8 6,7-Dimethoxy-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 50-00-0 formaldehyd 
• 138977-21-6 6,7-Dimethoxy-1-methyl-1H-isoquinoline-2-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 490-53-9 (+/-)-carnegine 
• 39487-50-8 6,7-dimethoxy-2-methyl-1-methylene-1,2,3,4-tetrahydroisoquinoline 
• 54193-08-7 (R)-salsolidine 
• 110527-65-6 N-methyl-N-(2-(3',4'-dimethoxyphenyl)ethyl)trifluoroacetamide 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 139750-86-0 (1S,S_R)-6,7-dimethoxy-1-(o-nitrophenylsulfinylmethyl)-1,2,3,4-tetrahydroisoquinoline 
• 109985-73-1 (R)-(Z)-N-methyl-N-<2-(2-(2'-(p-tolylsulfinyl)-1'-ethenyl)-4,5-dimethoxyphenyl)ethyl>trifluoroacetamide 
• 109985-71-9 N-methyl-N-(2-(2'-formyl-4',5'-dimethoxyphenyl)ethyl)trifluoroacetamide 

Relevant academic research and scientific papers

Online structural elucidation of alkaloids and other constituents in crude extracts and cultured cells of Nandina domestica by combination of LC-MS/MS, LC-NMR, and LC-CD analyses

The combination of NMR, MS, and CD data permitted the structural elucidation including the absolute configuration of the known alkaloids and unknown components in the extract matrix solution of Nandina domestica without isolation and sample purification p

Synthesis of Tetrahydroisoquinoline Alkaloids and Related Compounds through the Alkylation of Anodically Prepared α-Amino Nitriles

α-Amino nitrile 2a was conveniently prepared in two individual steps from chiral hexafluorophosphate salt isoquinolinium (-)-8b including anodic cyanation as an efficient means to activate the sp3 C1-H bond of the THIQ nucleus. The lithiation o

Enantioselective synthesis of chiral tetrahydroisoquinolines by iridium-catalyzed asymmetric hydrogenation of enamines

Chiral iridium complexes based on spiro phosphoramidite ligands are demonstrated to be highly efficient catalysts for the asymmetric hydrogenation of unfunctionalized enamines with an exocyclic double bond. In combination with excess iodine or potassium i

Asymmetric Intramolecular Allylic Amination: Straightforward Approach to Chiral C1-Substituted Tetrahydroisoquinolines

Newly introduced Pd-catalyzed asymmetric intramolecular allylic amination provides an easy access to pharmaceutically important 1-substituted tetrahydroisoquinolines. With this amination as the key step, (R)-carnegine was synthesized in an enantioselectiv

Chiral Acetylenic Sulfoxide in Enantioselective Synthesis of Tetrahydroisoquinoline and Tetrahydro-β-carboline Alkaloids. Total Synthesis of (R)-(+)-Carnegine and (R)-(+)-Tetrahydroharman

Michael addition of 2-(3,4-dimethoxyphenyl)ethylamine 3 or tryptamine 4 onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded the basic alkaloid skeleton of tetraisoquinoline and tetrahydro-β-carboline in high to moderate diastereoselectivity.Optically pure (R)-(+)-carnegine and (R)-(+)-tetrahydroharman have been synthesized.

NUCLEOPHILIC ADDITION TO HOMOCHIRAL N-ACYLISOQUINOLINIUM SALTS ASYMMETRIC SYNTHESIS OF (+)-CARNEGINE

The asymmetric addition of methyl nucleophiles to homochiral N-acylisoquinolinium salts was studied and utilized in a synthesis of the tetrahydroisoquinoline alkaloid, (+)-carnegine.

Chiral acetylenic sulfoxide in alkaloid synthesis. Total synthesis of (R)-(+)-carnegine

Remarkable diastereoselectivity was observed in the cyclization of β-aminovinyl sulfoxide 5a prepared from chiral acetylenic sulfoxide 1a in acidic medium. The cyclized product 6a was then converted to (R)-(+)-carnegine.

Stereochemistry of the Intermolecular and Intramolecular Conjugate Additions of Amines and Anions to Chiral (E)- and (Z)-Vinyl Sulfoxides. Total Syntheses of (R)-(+)-Carnegine and (+)- and (-)-Sedamine

The intramolecular addition of incipient amine anions to chiral (E)- and (Z)-vinyl sulfoxides occurs in the same diastereofacial sense, giving chiral isoquinoline and piperidine derivatives that differ in relative stereochemistry at C-2.In contrast, the conjugate addition reactions of (E)- and (Z)-β-styryl p-tolyl sulfoxide wih benzylamine and LiCH(CO2Et)2 are diastereoconvergent processes.The same major diastereomeric product is obtained in each case.We have attempted to rationalize the stereochemical outcome of the addition of nucleophiles to chiral vinyl sulfoxides according to the type of nucleophilic reagent employed (either chelating/hydrogen bonding or nonchelating) and from a consideration of possible transition states.

Asymmetric Intramolecular Conjugate Addition of Amines to Chiral Vinyl Sulphoxides. Total Synthesis of (R)-(+)-Carnegine

The (E)- and (Z)-vinyl sulphoxides (3) and (4) upon treatment with base, undergo cyclization to give chiral isoquinolines one of which was converted into (R)-(+)-carnegine.

Asymmetric Intramolecular Conjugate Addition of Amines to Chiral Vinyl Sulphoximides. Total Synthesis of (R)-(+)- and (S)-(-)-Carnegine

The chiral vinyl sulphoximides (3a) and (3b) upon treatment with base, undergo cyclization to give chiral isoquinolines which were converted into (R)-(+)- and (S)-(-)-carnegine.