6110-83-4

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 3851-29-4 2,3-(R,R)-11b-(S)-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetic acid methyl ester 
• 3332-90-9 (+/-)-(3c-ethyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2t-yl)-acetic acid methyl ester 
• 884337-46-6 4-[(S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]but-2-enoic acid ethyl ester 
• 884337-44-4 (S)-1-allyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 50919-08-9 1-(3',4'-Dimethoxyphenyl)ethylamine 
• 6110-83-4 (+/-)-(3t-ethyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2t-yl)-acetic acid-(3,4-dimethoxy-phenethylamide) 
• 181220-97-3 (S)-1-allyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 884337-48-8 (3-formyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl)acetic acid ethyl ester 
• 884337-49-9 (9,10-dimethoxy-3-vinyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl)acetic acid methyl ester 
• 884337-45-5 (S)-6,7-dimethoxy-1-(3-ethoxycarbonylallyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 

Downstream Products

• 523-01-3 (-)-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-ylmethyl)-3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline 
• 40752-81-6 rac-10,11,6',7'-tetramethoxy-emet-1'-ene 
• 483-18-1 emetine 
• 106066-83-5 ent-10,11,6',7'-tetramethoxy-emetan-2'-carboxylic acid anilide 
• 106066-83-5 rac-10,11,6',7'-tetramethoxy-emetan-2'-carboxylic acid anilide 
• 6110-83-4 (+/-)-(3c-ethyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2c-yl)-acetic acid-(3,4-dimethoxy-phenethylamide) 
• 40752-81-6 rac-10,11,6',7'-tetramethoxy-3αH-emet-1'-ene 
• 40752-81-6 rac-10,11,6',7'-tetramethoxy-2βH-emet-1'-ene 

Relevant academic research and scientific papers

Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step

Catalytic asymmetric allylation of 3,4-dihydro-6,7-dimethoxyisoquinoline was carried out using allyltrimethoxysilane in the presence of Cu(I) and tol-BINAP. The allyl adduct thus obtained was transformed to a chiral synthetic intermediate for (-)-emetine in good yield. The procedure was applied to the total synthesis of ent-emetine.

Enantioselective total syntheses of the Ipecacuanha alkaloid emetine, the Alangium alkaloid tubulosine and a novel benzoqainolizidine alkaloid by using a domino process

The first enantioselective syntheses of the Ipecacuanha alkaloid emetine (1) and the Alangium alkaloid tubulosine (2) is described employing a domino Knoevenagel/hetero-Diels-Alder reaction and an enantioselective catalytic transfer hydrogenation of imines as key steps. Thus, hydrogenation of the imine 15 with the catalyst (R,R)-16 gives the tetrahydroisoquinoline 14 with 95% ee which was transformed into the aldehyde (1S)-7. The three-component domino reaction of (1S)-7 with 6 and 8 led to 19, which in a second domino process was treated with K2CO3 in methanol followed by a hydrogenation to give the benzoquinolizidine 4 together with the diastereomers 22 and 23 in a overall yield of 66%. Further transformation of 4 with the amines 3 and 5 yielded enantiopure emetine (1) and tubulosine (2), respectively. In addition, starting from 19 the novel benzoquinolizidine alkaloid 34 was synthesised; this compound resembles the vallesiachotamine alkaloid dihydroantirhin 31, which has not been isolated so far but probably must also exist in nature.