2697-38-3

Upstream product

• 105-57-7 diethyl acetal 
• 63914-27-2 [2-(3,4-dimethoxy-phenyl)-ethyl]-carbamic acid benzyl ester 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 501-53-1 benzyl chloroformate 
• 3385-78-2 trimethyl indium 
• 191545-97-8 N-(carbobenzyloxy)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines

Triorganoindium reagents (R3In) react with tetrahydroisoquinolines (THIQs) in the presence of Ph3CBF4 as an oxidant to afford 1-substituted THIQs. The reaction proceeds in good yields at rt using 50 mol % R3In with a variety of organic groups. 1H NMR studies show the generation of an iminium ion intermediate, supporting a two-step mechanism based on THIQ oxidation and R3In nucleophilic addition. This reaction was applied to the synthesis of the alkaloid nuciferine in three steps.

Total synthesis of bernumicine and bernumidine, two alkaloids from Berberis nummularia

Bernumicine and bernumidine are two alkaloids extracted from Berberis nummularia. Their total synthesis has been completed and it has been shown that the configuration of the stereogenic carbon of both is (R).