4781-58-2

Upstream product

• 104621-41-2 (Z)-7-Acetoxy-1-<(3-acetoxy-4-methoxyphenyl)methylene>-2-acetyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 74-88-4 methyl iodide 

Downstream Products

• 76318-96-2 C₁₈⁽¹⁴⁾CH₂₃NO₄ 
• 72258-91-4 1,2-dehydronorreticuline 
• 13168-51-9 N-benzoyl-norreticuline 
• 57231-35-3 4',6-O,O-dimethylpapaveroline 
• 72072-54-9 (S)-6,7-dihydroxy-1-(3',4'-dihydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide 
• 18694-10-5 1-(3'-hydroxy-4'-methoxybenzyl)-6,7-dimethoxyisoquinoline 
• 21411-21-2 1,2-dehydroreticulinium iodide 
• 485-19-8 (+)-(S)-reticuline 

Relevant academic research and scientific papers

Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.