149355-79-3

Upstream product

• 75-36-5 acetyl chloride 
• 149378-57-4 3,11-dihydroxy-14-(3-hydroxy-4-methoxyphenyl)-2,12-dimethoxy-8,9-dihydro-6H-[1]benzopyrano-[4′,3′:4,5]pyrrolo-[2,1-a]isoquinolin-6-one 
• 621-59-0 isovanillin 
• 36455-21-7 3-benzyloxy-4-methoxyphenylethylamine 
• 121-33-5 vanillin 
• 63909-29-5 (E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene 
• 5487-33-2 O-benzylhomoisovanillic acid 
• 21411-26-7 N-[3-(benzyloxy)-4-methoxyphenethyl]-2-[3-(benzyloxy)-4-methoxyphenyl]acetamide 
• 680189-48-4 ethyl 8-(benzyloxy)-1-(3-(benzyloxy)-4-methoxyphenyl)-2-(2,4-bis(benzyloxy)-5-methoxyphenyl)-9-methoxy-5,6-dihydropyrrolo-[2,1-a]isoquinoline-3-carboxylate 
• 680189-50-8 2-(2,4-dihydroxy-5-methoxy-phenyl)-8-hydroxy-1-(3-hydroxy-4-methoxy-phenyl)-9-methoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 1034028-91-5 (Z)-ethyl 2,4-bis(benzyloxy)-5-methoxy-α-nitrocinnamate 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 21411-27-8 6-(benzyloxy)-1-[3-(benzyloxy)-4-methoxybenzyl]-7-methoxy-3,4-dihydroisoquinoline 
• 54313-33-6 2-(3-(benzyloxy)-4-methoxyphenyl)acetyl chloride 

Downstream Products

• 149379-26-0 3,11-dihydroxy-14-(3-hydroxy-4-methoxyphenyl)-2,12-dimethoxy-6H-[1]benzopyrano-[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 149355-77-1 3,11-bis(acetoxy)-14-(3-acetoxy-4-methoxyphenyl)-2,12-dimethoxy-6H-[1]benzopyrano[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.