220230-71-7

Upstream product

• 1144503-25-2 dimethyl N-benzyl-3,4-bis(4,5-dimethoxy-2-methoxymethoxyphenyl)pyrrole-2,5-dicarboxylate 
• 220230-68-2 1,2-bis(4,5-dimethoxy-2-(methoxymethoxy)phenyl)acetylene 
• 129103-69-1 2-bromo-4,5-dimethoxyphenol 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 220230-70-6 dimethyl 4,5-bis(4,5-dimethoxy-2-(methoxymethoxy)phenyl)-1,2-diazine-3,6-dicarboxylate 
• 169776-14-1 1-bromo-4,5-dimethoxy-2-(methoxymethoxy)benzene 

Downstream Products

• 220230-73-9 methyl 7,8-dimethoxy-1-(4,5-dimethoxy-2-hydroxyphenyl)-<1>-benzopyrano<3,4-b>pyrrol-4(3H)-one-2-carboxylate 

Relevant academic research and scientific papers

A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2, 5-dicarboxylates

A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2, 5-dicarboxylates (3) has been developed. The key reactions involved are the Hinsberg-type synthesis of dimethyl N-benzyl-3,4-dihydroxypyrrole-2,5- dicarboxylate (6) followed by palladium-catalyzed Suzuki-Miyaura coupling of its bis-triflate derivative (7). The N-benzyl protecting group of the resulting 3,4-diaryl pyrrole-2,5-dicarboxyl ates (8) is cleanly removed under hydrogenolytic or solvolytic conditions.

Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels - Alder reactions

Concise, efficient total syntheses of ningalin A (1), lamellarin O (2), lukianol A (3), and permethyl storniamide A (5) are detailed on the basis of a common heterocyclic azadiene Diels-Alder strategy (1,2,4,5-tetrazine → 1,2-diazine → pyrrole) ideally suited for construction of the densely functionalized pyrrole cores found in the three classes of marine natural products. Examination of the natural products and a number of synthetic intermediates revealed that some including lamellarin O (2) and lukianol A (3) exhibit modest cytotoxic activity against both wild-type and multidrug- resistant tumor cell lines. Fundamentally more important, a new class of agents including permethyl storniamide A (5) and its precursor 30, which lack inherent cytotoxic activity, are disclosed which 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.