187156-50-9

Upstream product

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 121-33-5 vanillin 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 118474-94-5 (E)-1-nitro-2-(2',3',4'-trimethoxyphenyl)ethene 
• 24237-31-8 N-<2-(2,3,4-trimethoxyphenyl)ethyl>-2-(3,4-dimethoxyphenyl)acetamide 
• 3937-16-4 2-(2,3,4-trimethoxyphenyl)ethylamine 
• 47539-89-9 5,6,7-trimethoxy-1-(3',4'-dimethoxybenzyl)3,4-dihydroisoquinoline 
• 919082-31-8 ethyl 1-(3,4-dimethoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-7,8,9-trimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 
• 75-36-5 acetyl chloride 
• 149355-75-9 14-(3,4-dimethoxyphenyl)-3-hydroxy-2,10,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4’,3’:4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 1034028-91-5 (Z)-ethyl 2,4-bis(benzyloxy)-5-methoxy-α-nitrocinnamate 

Downstream Products

• 919082-44-3 14-(3,4-dimethoxyphenyl)-3-acetoxy-2,10,11,12-tetramethoxy-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.