181423-71-2

Basic information

• Product Name: Lamellarine S
• CAS NO: 181423-71-2
• Molecular Weight: 543.573
• Mol File: 181423-71-2.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: Lamellarine S(CAS DataBase Reference)
• NIST Chemistry Reference: Lamellarine S(181423-71-2)
• EPA Substance Registry System: Lamellarine S(181423-71-2)

Safety Data

• Hazardous Substances Data: 181423-71-2(Hazardous Substances Data)

Upstream product

• 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 
• 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 
• 681431-19-6 2-hydroxy-4,5-dimethoxyphenylboronic acid 
• 681431-25-4 2-bromo-1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 1034028-87-9 (Z)-ethyl 2-benzyloxy-4,5-dimethoxy-α-nitrocinnamate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 433267-55-1 4-bromo-1H-pyrrole-2-carboxylic acid ethyl ester 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 321681-28-1 2-bromo-1-(2-bromo-4,5-dimethoxyphenyl)-ethanone 
• 5884-22-0 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride 

Relevant articles and documents

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

Application of differential reactivity towards synthesis of lamellarin and 8-oxoprotoberberine derivatives: Study of photochemical properties of aryl-substituted benzofuran-8-oxoprotoberberines

A unique differential reactivity between dihydroisoquinolines and 3-nitrocoumarins was observed and was exploited for the efficient construction of lamellarins and their isomeric benzofuran-8-oxoprotoberberine derivatives under acid-catalyzed or base-promoted conditions. Further, these prepared aryl-substituted benzofuran-8-oxoprotoberberine derivatives bearing electron-donating substituents on benzofuran moiety are found to be benchtop stable but light-sensitive, and can undergo oxidative ring-opening reaction to give the corresponding keto products when exposed to visible light under aerobic conditions.

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.