681431-23-2

Upstream product

• 681431-20-9 2-[2-(2-bromo-4,5-dimethoxyphenyl)ethoxy]tetrahydro-2H-pyran 
• 516465-80-8 4-bromo-1H-pyrrole-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 
• 433267-55-1 4-bromo-1H-pyrrole-2-carboxylic acid ethyl ester 
• 289507-36-4 2-(2-bromo-4,5-dimethoxyphenyl)ethyl alcohol 
• 127572-59-2 4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 681431-18-5 2-(2-hydroxyethyl)-4,5-dimethoxyphenylboronic acid 
• 681431-22-1 5-bromo-4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester 

Downstream Products

• 919082-30-7 ethyl 1,2-bis(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 
• 681431-25-4 2-bromo-1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 681431-24-3 1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 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

A Modular Synthesis of the Lamellarins: Total Synthesis of Lamellarin G Trimethyl Ether

A modular synthesis of the lamellarin family of natural products has been developed that is based on the application of three iterative halogenation/cross-coupling reaction sequences. The ability to halogenate the pyrrole core in a regioselective fashion, even in the presence of highly electron-rich aryl substituents, has been established. The compatibility of Suzuki coupling conditions with free alcohols and phenols in the boronic acids has been employed to reduce the number of protection/deprotection steps. Indeed, the presence of a free phenol on boronic acid 3 has been determined to be critical for the successful final coupling in route to lamellarin G trimethyl ether, since protected versions fail to undergo coupling.