53392-66-8

Upstream product

• 94757-36-5 4,5,3',4'-tetramethoxy-2-vinyl-stilbene 
• 4747-98-2 S-(-)-Norlaudanosine 
• 57651-56-6 (S)-1-<(3,4-Dimethoxyphenyl)methyl>-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 6957-27-3 3,4-dihydropapaverine 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 1344118-31-5 (S)-(+)-1-(2-bromo-4,5-dimethoxybenzyl)-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 53207-00-4 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene 
• 30045-07-9 2-methyl-6,7-dimethoxy-3,4-dihydroisoquinolinium iodide 

Relevant academic research and scientific papers

Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile

Under controlled conditions, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline- 1-carbonitrile can be quantitatively deprotonated in the α-position. Its alkylation directly furnishes 3,4-dihydroisoquinolines which can serve as starting materials for the preparation of various alkaloids. Here, the preparation of the benzylisoquinolines (+)-laudanidine, (+)-armepavine, and (+)-laudanosine as well as the tetrahydroprotoberberines ( - )-corytenchine and ( - )-tetrahydropseudoepiberberine using Noyori's asymmetric transfer hydrogenation are described. The dimeric alkaloids (+)-O-methylthalibrine and (+)-tetramethylmagnolamine were obtained from nonracemic precursors in Ullmann diaryl ether syntheses.

Novel Zinc-Promoted Alkylation of Iminium Salts. New Synthesis of Benzylisoquinoline, Phthalidylisoquinoline, and Protoberberine Alkaloids and Related Compounds

Zinc-promoted reductive coupling reaction of iminium salts with alkyl halides was found to be a successful key reaction for synthesis of a variety of alkaloids such as benzylisoquinoline, phthalidylisoquinoline, and protoberberine alkaloids.More specifically, laudanosine, cordrastine, hydrastine, narcotine, tetrahydropalmatine, and canadine were obtained.A new route for the synthesis of the emetine and yohimbine skeletons was exploited.

ELECTROREDUCTIVE SYNTHESIS OF 1-(BROMOBENZYL)-ISOQUINOLINE DERIVATIVES AND ITS APPLICATION TO CULARINE SYNTHESIS

Electrochemical reduction of immonium salts in the presence of bromobenzylbromide derivatives gave 1-(bromobenzyl)-isoquinoline derivatives in moderate yields.This reaction is useful in the synthesis of several natural alkaloids as exemplified in the synt