53602-52-1

Upstream product

• 73357-18-3 (4,5-dimethoxy-2-nitrophenyl)acetic acid 

Downstream Products

• 79831-93-9 4,5-dimethoxy-2-nitro-N-(3,4,5-trimethoxyphenethyl)phenylacetamide 
• 20824-18-4 protostephanone 
• 549-28-0 protostephanine 
• 79832-27-2 1-(4,5-dimethoxy-2-nitrobenzyl)-3,4-dihydro-6,7,8-trimethoxyisoquinoline methiodide 
• 79832-04-5 4,5-Dimethoxy-2-(6,7,8-trimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-phenylamine 
• 79832-10-3 1-(4,5-dimethoxy-2-nitrobenzyl)-3,4-dihydro-6,7,8-trimethoxyisoquinoline 
• 79832-06-7 1-(4,5-dimethoxy-2-nitrobenzyl)-1,2,3,4-tetrahydro-6,7,8-trimethoxy-2-methylisoquinoline 
• 20323-72-2 (6,7-dimethoxyisoquinolin-1-yl)(4,5-dimethoxy-2-nitrophenyl)-methanone 
• 16408-78-9 dicentrinone 
• 16251-41-5 1-(2'-nitro-4',5'-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 2129-52-4 N-(3,4-dimethoxyphenethyl)-2-(4,5-dimethoxy-2-nitrophenyl)-acetamide 

Relevant academic research and scientific papers

Synthesis along Biosynthetic Pathways. Part 2. Synthesis of Protostephanine

The dienone protostephanone (3) is synthesised by phenol coupling or by Pschorr cyclisation from readily prepared tetrahydroisoquinolines, and the corresponding dienols (17) and (18) are converted by rearrangement, fragmentation, and reduction into protostephanine (4).This sequence mimics the natural pathway to the alkaloid.

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.