52336-73-9

Upstream product

• 22231-61-4 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine 
• 100-39-0 benzyl bromide 
• 121-33-5 vanillin 
• 63909-38-6 1-(benzyloxy)-2-methoxy-4-[(E)-2-nitroethenyl]benzene 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 55803-41-3 N-formyl-2-[3-methoxy-4-(benzyloxy)phenyl]ethylamine 
• 15357-92-3 6-methoxy-7-(benzyloxy)-3,4-dihydroisoquinoline 
• 74-88-4 methyl iodide 

Downstream Products

• 436-05-5 (±)-curine 
• 92172-57-1 7-benzyloxy-6-methoxy-1-(2-amino-6-methoxybenzyl)-1,2,3,4-tetrahydro-2-methylisoquinoline 

Relevant academic research and scientific papers

A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine

Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.

Synthesis of Benzylisoquinoline Derivatives

4-Benzyloxy-3-methoxyphenethylamine (1) on formylation with ethyl formate gave N-formyl-7-benzyloxy-6-methoxyphenethylamine (2) which on Bischeler-Napieralski cyclization with phosphorusoxychloride followed by methylation with methyl iodide furnished 7-be