168010-02-4

Upstream product

• 186837-20-7 3,4-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-triisopropylsilanyl-1H-pyrrole-2-carboxylic acid methyl ester 
• 1003856-48-1 methyl 3,4-bis(4-isopropoxyphenyl)pyrrole-2-carboxylate 
• 1418216-87-1 2,3-bis[4-(benzyloxy)phenyl]succinonitrile 
• 838-96-0 2-[4-(benzyloxy)phenyl]acetonitrile 
• 1418216-89-3 3,4-bis[4-(benzyloxy)phenyl]-1H-pyrrole 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 1418216-90-6 methyl 3,4-bis(4-(benzyloxy)phenyl)-1H-pyrrole-2-carboxylate 
• 1418216-86-0 2,3-bis[4-(benzyloxy)phenyl]acrylonitrile 
• 14191-95-8 4-cyanomethylphenol 
• 50690-53-4 2-[4-(propan-2-yloxy)phenyl]acetonitrile 
• 6967-88-0 1-bromo-4-isopropoxybenzene 
• 170238-94-5 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 246868-68-8 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester 
• 186837-19-4 3,4-Dibromo-1-triisopropylsilanyl-1H-pyrrole-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Solid-phase synthesis of lamellarins Q and O

An efficient solid phase synthesis of the pyrrole-based alkaloids lamellarins Q and O using Merrifield resin and N-protected methyl 3,4-dibromopyrrole-2-carboxylate as a scaffold is described.

Formation of 3,4-Diarylpyrrole- and Pyrrolocoumarin Core of Natural Marine Products via Barton–Zard Reaction and Selective O-Demethylation

A metal-free approach to 3,4-diarylpyrrole-2-carboxylate and pyrrolocoumarin cores of lamellarins and related natural products based on Barton–Zard reaction of nitrostilbenes with ethyl isocyanoacetate was developed. In the case of diarylpyrrole-2-carboxy

Synthesis of lamellarin alkaloids using orthoester-masked α-keto acids

Pyruvic acid and other α-keto acids are frequently encountered as intermediates in metabolic pathways, yet their application in total synthesis has met with limited success. In this work, we present a bioinspired strategy that utilizes highly functionaliz

A Paal-Knorr approach to 3,4-diaryl-substituted pyrroles: Facile synthesis of lamellarins O and Q

A very simple, yet efficient synthetic methodology, to obtain 3,4-diaryl-substituted pyrroles is described. The approach is based on the Knoevenagel condensation between arylacetonitriles and substituted aromatic aldehydes, followed by conjugate addition of cyanide to afford succinonitriles in excellent yields. The products thus obtained were subjected to DIBAL-H reduction, followed by cyclization under acidic conditions to produce the corresponding pyrroles in good overall yields. The utility of this protocol is exemplified by the synthesis of the marine alkaloids lamellarins O and Q.

Palladium-catalyzed cross-coupling of N-benzenesulfonyl-3,4-dibromopyrrole and its application to the total syntheses of lamellarins O, P, Q, and R

Palladium-catalyzed Suzuki-Miyaura coupling of N-benzenesulfonyl-3,4-dibromopyrrole with a variety of arylboronic acids gave the corresponding 3,4-diarylpyrroles in high yields. The 3,4-differentially arylated pyrroles could also be prepared by stepwise cross-coupling approach. The total syntheses of lamellarins O, P, Q, and R have been achieved by using the cross-coupling and the directed lithiation as key reactions.

Convergent syntheses of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners

The marine alkaloids lamellarin-Q 1, lamellarin-O 2 and lukianol-A 3 as well as their more highly oxygenated congeners 22 and 23 are synthesised using Stille, Suzuki or Negishi cross-coupling reactions as the key step.