858520-87-3

Upstream product

• 6957-27-3 3,4-dihydropapaverine 
• 1034028-91-5 (Z)-ethyl 2,4-bis(benzyloxy)-5-methoxy-α-nitrocinnamate 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 7298-50-2 2,4-bis-(benzyloxy)-5-methoxybenzaldehyde 
• 121-33-5 vanillin 

Downstream Products

• 919082-41-0 14-(3,4-dimethoxyphenyl)-3-acetoxy-2,11,12-trimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 919082-47-6 14-(3,4-dimethoxyphenyl)-3-acetoxy-2,11,12-trimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 858520-89-5 14-(3,4-dimethoxyphenyl)-3-hydroxy-2,11,12-trimethoxy-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.

Utility of polymer-supported reagents in the total synthesis of lamellarins

Four solid-supported reagents have been utilized in the multistep synthesis of lamellarins. The use of Amberlyst A-26 Br3- and polymer bound pyridine hydrobromide perbromide (PVPHP) for keto α-bromination of the less studied ortho-su