266674-76-4

Upstream product

• 1265221-55-3 C₈H₈INO₄ 
• 1265221-56-4 C₁₅H₁₃NO₆ 
• 1265221-57-5 C₁₅H₁₂BrNO₆ 
• 1265221-58-6 C₂₅H₂₄BrNO₈ 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 1265221-54-2 dimethyl 3,4-diiodo-1H-pyrrole-2,5-dicarboxylate 
• 1757-29-5 1H-pyrrole-2,5-dicarboxylic acid dimethyl ester 
• 473401-82-0 pyrrole-1,2,5-tricarboxylic acid 1-tert-butyl ester 2,5-dimethyl ester 
• 266674-74-2 dimethyl 3-(4,5-dimethoxy-2-(methoxymethoxy)phenyl)-4-(3,4-dimethoxyphenyl)pyrrole-2,5-dicarboxylate 
• 266674-73-1 dimethyl 4-(4,5-dimethoxy-2-(methoxymethoxy)phenyl)-5-(3,4-dimethoxyphenyl)-1,2-diazine-3,6-dicarboxylate 
• 266674-72-0 2-[(3,4-dimethoxyphenyl)ethynyl]-4,5-dimethoxy-1-(methoxymethoxy)benzene 
• 266674-80-0 2-(3,4-dimethoxy-phenylethynyl)-4,5-dimethoxy-phenol 
• 266674-71-9 2-[(3,4-dimethoxyphenyl)ethynyl]-4,5-dimethoxybenzaldehyde 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 

Downstream Products

• 266674-77-5 7,8-dimethoxy-3-(2-(3,4-dimethoxyphenyl)ethyl)-1-(3,4-dimethoxyphenyl)-[1]-benzopyrano[3,4-b]pyrrol-4(3H)-one-2-carboxylic acid 
• 266674-78-6 1-(3,4-dimethoxyphenyl)-3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxy-4-oxo-3H-[1]benzopyrano[3,4-b]pyrrole-4-one 
• 181423-71-2 14-(3,4-dimethoxyphenyl)-2,3,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 

Relevant academic research and scientific papers

Modular total syntheses of lamellarin G trimethyl ether and lamellarin S

Modular total syntheses of the title compounds 2 and 3 are reported. The key pyrrolic building block 8 was prepared from the readily accessible pyrrole 6 via a di-iodination/mono-deiodination sequence. Suzuki-Miyaura cross-coupling of compound 8 with boronate ester 9 afforded lactone 10. Bromination of compound 10 followed by N-alkylation under Mitsunobu conditions afforded the fully substituted pyrrole 13 that engaged in a second Suzuki-Miyaura cross-coupling reaction with boronic acid 14 to give compound 15. Hydrolysis of the ester moiety within the last compound afforded acid 16 that engaged in a decarboxylative Heck cyclization process to give lamellarin G trimethyl ether (3). A related sequence of reactions starting from building block 8 and using the isopropoxy-substituted arenes 22, 25 and 27 has allowed for the completion of the first total synthesis of lamellarin S (2). The first total synthesis of the marine alkaloid lamellarin S is described.

Short and flexible route to 3,4-diarylpyrrole marine alkaloids: Syntheses of permethyl storniamide A, ningalin B, and lamellarin G trimethyl ether

A highly efficient route to 3,4-diarylpyrrole marine alkaloids has been developed using Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki cross-coupling of the 3,4-dihydroxypyrrole bis-triflate derivatives as key reactions. Based on this approach, formal syntheses of permethyl storniamide A and ningalin B, and a total synthesis of lamellarin G trimethyl ether have been achieved.

Total synthesis of Ningalin B utilizing a heterocyclic azadiene Diels- Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents

A concise, efficient approach to the total synthesis of ningalin B (1) based on a heterocyclic azadiene Diels-Alder strategy (1,2,4,5-tetrazine → 1,2-diazine → pyrrole) ideally suited for construction of the densely functionalized pyrrole core found in the natural product is detailed. Examination of the natural product and a number of synthetic intermediates revealed that while lacking inherent cytotoxic activity, many reverse the multidrug-resistant (MDR) phenotype, resensitizing a human colon cancer cell line (HCT116/VM46) to vinblastine and doxorubicin at lower doses than the prototypical agent verapamil.