523-01-3

Upstream product

• 6110-83-4 2,3-(R,R)-11b-(S)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetamide 
• 40752-81-6 rac-10,11,6',7'-tetramethoxy-emet-1'-ene 
• 50919-08-9 1-(3',4'-Dimethoxyphenyl)ethylamine 
• 6110-83-4 (+/-)-(3c-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) 
• 120-20-7 2-(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) 
• 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) 
• 74059-26-0 (2S,3S,11bS)-2-(6,7-Dimethoxy-3,4-dihydro-isoquinolin-1-ylmethyl)-3-ethyl-9,10-dimethoxy-1,2,3,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-4-one 
• 108-55-4 glutaric anhydride, 
• 4773-45-9 9,10-dimethoxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one 
• 74059-24-8 (2S,11bS)-2-(6,7-Dimethoxy-3,4-dihydro-isoquinolin-1-ylmethyl)-9,10-dimethoxy-4-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid methyl ester 
• 74064-93-0 (2S,11bS)-2-(6,7-Dimethoxy-3,4-dihydro-isoquinolin-1-ylmethyl)-3-ethyl-9,10-dimethoxy-4-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid methyl ester 
• 74059-25-9 (2S,11bS)-2-(6,7-Dimethoxy-3,4-dihydro-isoquinolin-1-ylmethyl)-3-ethyl-9,10-dimethoxy-4-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid 
• 74059-32-8 1,2,3,6,7,11b-hexahydro-9,10-dimethoxy-3-methoxycarbonyl-3-phenylselenobenzoquinolizin-4-one 

Downstream Products

• 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 

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.

THE TOTAL STEREOSELECTIVE RETRO MASS SPECTRAL SYNTHESIS OF (+/-)-EMETINE

A new route to (+/-)-emetine (18) via the Michael addition product (4A) is described.Addition of 3,4-dihydro-6,7-dimethoxy-1-methylisoquinoline (3) to the α,β-unsaturated ester (2) afforded 2-(3',4'-dihydro-6',7'-dimethoxy-1'-isoquinolinylmethyl)-3-methoxycarbonyl-1,2,3,6,7,11b-hexahydro-9,10-dimethoxybenzoquinolizin-4-one (4A) which was converted to (+/-)-emetine in 6 steps.