66408-37-5

Upstream product

• 66408-34-2 6-(7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-5-carbonyl)-2,3-dimethoxy-benzoic acid 
• 74-88-4 methyl iodide 
• 71733-96-5 9,10,13a-trimethoxy-2,3-(methylenedioxy)-8,13-dioxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine 
• 71766-69-3 13a-hydroxy-9,10-dimethoxy-2,3-(methylenedioxy)-8,13-dioxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine 
• 66408-38-6 1-(2-carboxy-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinoline 
• 62595-72-6 berberinephenolbetaine 
• 75509-67-0 3,4-dihydro-(3,4-dimethoxy-2-methoxycarbonylbenzoyl)-6,7-(methylenedioxy)isoquinoline 

Downstream Products

• 71734-53-7 1,2,3,4-tetrahydro-1-(3,4-dimethoxy-2-methoxycarbonylbenzoyl)-2-methyl-6,7-(methylenedioxy)isoquinoline 

Relevant academic research and scientific papers

Reaction of Protoberberine-type Alkaloids. Part 13. Biogenetic Conversion of Protoberberine Alkaloids into Phthalideisoquinoline Alkaloids

A new convenient and biogenetic-type conversion of the protoberberine alkaloids into the phthalideisoquinoline alkaloids is described.The phthalideisoquinoline 5,6-dimethoxy-3-(6,7-dimethoxyisoquinolin-1-yl)isobenzofuran-1(3H)-one (4) was derived from 8-norcoralyne chloride (1) via 13-oxidonorcoralyne (3) in a one-pot reaction consisting of dye-sensitized photo-oxygenation followed by treatment with sodium borohydride.The conversion of berberine chloride into (+/-)-β-hydrastine (21) was performed by a reaction sequence involving conversion of 8,13a-epidioxy-9,10-dimethoxy- 2,3-methylenedioxy-13-oxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine (9) into 1-(2-carboxy-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinoline (11) using pyridinium chloride, followed by methylation and reductive cyclization.