919082-39-6

Upstream product

• 806600-50-0 6-(benzyloxy)-1-[4-(benzyloxy)-3-methoxybenzyl]-7-methoxy-3,4-dihydroisoquinoline 
• 1034028-91-5 (Z)-ethyl 2,4-bis(benzyloxy)-5-methoxy-α-nitrocinnamate 
• 4672-96-2 2-[4-(benzyloxy)-3-methoxyphenyl]-N-[3-(benzyloxy)-4-methoxyphenethyl]acetamide 
• 36455-21-7 3-benzyloxy-4-methoxyphenylethylamine 
• 121-33-5 vanillin 
• 100-39-0 benzyl bromide 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 63909-29-5 (E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene 
• 621-59-0 isovanillin 

Downstream Products

• 97614-65-8 lamellarin D 
• 97633-82-4 14-(4-acetoxy-3-methoxyphenyl)-3,11-diacetoxy-2,12-dimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 656836-79-2 14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 660396-68-9 14-(4-acetoxy-3-methoxyphenyl)-3,11-diacetoxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 

Relevant academic research and scientific papers

Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings

(Chemical Equation Presented) Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and α-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.