919082-30-7

Basic information

• Product Name: Pyrrolo[2,1-a]isoquinoline-3-carboxylic acid, 1,2-bis(3,4-dimethoxyphenyl)-5,6-dihydro-8,9-dimethoxy-, ethyl ester
• CAS NO: 919082-30-7
• Molecular Formula: C33H35NO8
• Molecular Weight: 573.643
• Mol File: 919082-30-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Pyrrolo[2,1-a]isoquinoline-3-carboxylic acid, 1,2-bis(3,4-dimethoxyphenyl)-5,6-dihydro-8,9-dimethoxy-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolo[2,1-a]isoquinoline-3-carboxylic acid, 1,2-bis(3,4-dimethoxyphenyl)-5,6-dihydro-8,9-dimethoxy-, ethyl ester(919082-30-7)
• EPA Substance Registry System: Pyrrolo[2,1-a]isoquinoline-3-carboxylic acid, 1,2-bis(3,4-dimethoxyphenyl)-5,6-dihydro-8,9-dimethoxy-, ethyl ester(919082-30-7)

Safety Data

• Hazardous Substances Data: 919082-30-7(Hazardous Substances Data)

Upstream product

• 681431-26-5 4-(3,4-dimethoxy-phenyl)-5-{4,5-dimethoxy-2-[2-(toluene-4-sulfonyloxy)-ethyl]-phenyl}-1H-pyrrole-2-carboxylic acid ethyl ester 
• 681431-23-2 4-(3,4-dimethoxyphenyl)-5-[2-(2-hydroxyethyl)-4,5-dimethoxyphenyl]-1H-pyrrole-2-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 
• 681431-20-9 2-[2-(2-bromo-4,5-dimethoxyphenyl)ethoxy]tetrahydro-2H-pyran 
• 681431-22-1 5-bromo-4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester 
• 681431-18-5 2-(2-hydroxyethyl)-4,5-dimethoxyphenylboronic acid 
• 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 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 

Downstream Products

• 1026618-82-5 C₃₁H₃₁NO₈ 

Relevant articles and documents

Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated α-aminonitrile

(Chemical Equation Presented) 1,2,3,4-Tetrahydroisoquinoline-1- carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions which would be cleaved under the harsh conditions of the classical Bischler-Napieralski reaction.

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.