858520-89-5

Upstream product

• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 7298-50-2 2,4-bis-(benzyloxy)-5-methoxybenzaldehyde 
• 1034028-91-5 (Z)-ethyl 2,4-bis(benzyloxy)-5-methoxy-α-nitrocinnamate 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 6957-27-3 3,4-dihydropapaverine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 858520-87-3 ethyl 1-(3,4-dimethoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 

Downstream Products

• 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 
• 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 

Relevant academic research and scientific papers

Scalable Total Syntheses of Some Natural and Unnatural Lamellarins: Application of a One-Pot Domino Process for Regioselective Access to the Central 1,2,4-Trisubstituted Pyrrole Core

Short and scalable total syntheses of lamellarin G trimethyl ether, lamellarin D trimethyl ether, lamellarin H, lamellarin ?, dihydrolamellarin ?, and lamellarin U have been realized in four to six linear steps with an overall yield of ≤22%. Highlights of

A high-yielding modular access to the lamellarins: Synthesis of lamellarin G trimethyl ether, lamellarin η and dihydrolamellarin η

A deprotonated α-aminonitrile serves as a key intermediate in a highly efficient (95 % per step on average; see scheme) modular synthetic approach to the lamellarin alkaloids. Its reaction with an α,β- unsaturated aldehyde forms the central pyrrole ring in a one-pot procedure. The construction of the fused pentacyclic skeleton is completed by a microwave-assisted Ullmann-type lactone formation.

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