Short and Efficient Syntheses of Protoberberine Alkaloids using Palladium-Catalyzed Enolate Arylation.

Short and Efficient Syntheses of Protoberberine Alkaloids using Palladium-Catalyzed Enolate Arylation.

A concise synthesis of the biologically active alkaloid berberine is reported, and a versatile palladium-catalyzed enolate arylation is used to form the isoquinoline core. The overall yield of 50 % is a large improvement over the single, previous synthesis. By design, this modular route allows the r...

Bibliografski detalji
Glavni autori:	Gatland, A, Pilgrim, B, Procopiou, P, Donohoe, T
Format:	Journal article
Jezik:	English
Izdano:	Wiley 2014

Slični predmeti

Palladium-catalyzed enolate arylation as a key C-C bond-forming reaction for the synthesis of isoquinolines.
od: Pilgrim, B, i dr.
Izdano: (2015)

Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization.
od: Pilgrim, B, i dr.
Izdano: (2013)

Palladium-catalysed enolate arylation in the synthesis of isoquinolines
od: Gatland, A, i dr.
Izdano: (2014)

Expedient synthesis of substituted aromatics via the alpha-arylation of enolates
od: Pilgrim, B, i dr.
Izdano: (2013)

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones.
od: Donohoe, T, i dr.
Izdano: (2012)

Palladium-catalyzed intramolecular O-arylation of enolates: application to benzo[b]furan synthesis.
od: Willis, M, i dr.
Izdano: (2004)

Protoberberine Isoquinoline Alkaloids from Arcangelisia gusanlung
od: Ling-Ling Yu, i dr.
Izdano: (2014-08-01)

Palladium-catalyzed aryl halide carbonylation-intramolecular O-enolate acylation: efficient isocoumarin synthesis, including the synthesis of thunberginol A.
od: Tadd, A, i dr.
Izdano: (2009)

Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes
od: Willis, M, i dr.
Izdano: (2006)

Palladium catalysed aryl enol ether synthesis from vinyl triflates.
od: Willis, M, i dr.
Izdano: (2003)

Palladium-catalysed enolate arylation in the synthesis of aromatic heterocycles and substituted heterocycles
od: Esteves, C
Izdano: (2017)

Palladium-catalyzed aminosulfonylation of aryl halides.
od: Nguyen, B, i dr.
Izdano: (2010)

Palladium-Catalyzed Esterification of Aryl Fluorosulfates with Aryl Formates
od: Xue Chen, i dr.
Izdano: (2024-04-01)

Palladium-catalyzed α-arylation of carbonyls in the de novo synthesis of aromatic heterocycles.
od: Potukuchi, H, i dr.
Izdano: (2015)

Efficient palladium-catalysed enamide synthesis from enol triflates and enol tosylates
od: Willis, M, i dr.
Izdano: (2005)

Entropy-Driven Inclusion of Natural Protoberberine Alkaloids in Sulfobutylether-β-Cyclodextrin
od: Zsombor Miskolczy, i dr.
Izdano: (2022-11-01)

Analysis of the Coptis chinensis genome reveals the diversification of protoberberine-type alkaloids
od: Yifei Liu, i dr.
Izdano: (2021-06-01)

The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
od: Cho, Eun Jin, i dr.
Izdano: (2013)

Palladium-catalyzed alpha-arylation of oxindoles.
od: Durbin, M, i dr.
Izdano: (2008)

Benzo[b]furan synthesis via palladium-catailysed intramolecular o-arylation of enolates.
od: Taylor, D, i dr.
Izdano: (2005)

Catalytic enolate arylation with 3-bromoindoles allows the formation of β-carbolines.
od: Alves Esteves, C, i dr.
Izdano: (2017)

Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids
od: Helfried Neumann, i dr.
Izdano: (2020-07-01)

Palladium-Catalyzed Synthesis of N-Aryl Carbamates
od: Fors, Brett P., i dr.
Izdano: (2015)

A concise enzyme cascade enables the manufacture of natural and halogenated protoberberine alkaloids
od: Fei Li, i dr.
Izdano: (2025-02-01)

De novo production of protoberberine and benzophenanthridine alkaloids through metabolic engineering of yeast
od: Xiang Jiao, i dr.
Izdano: (2024-10-01)

Neuroprotective role of a protoberberine alkaloid against aluminum-induced neuroinflammation and excitotoxicity
od: Ratna BABURAJ, i dr.
Izdano: (2023-06-01)

Palladium(0)-Catalyzed Arylative Dearomatization of Phenols
od: Rousseaux, Sophie, i dr.
Izdano: (2013)

Palladium-Catalyzed N-Arylation of 2-Aminothiazoles
od: McGowan, Meredeth A., i dr.
Izdano: (2013)

Palladium(0)-catalyzed arylative dearomatization of phenols.
od: Rousseaux, S, i dr.
Izdano: (2011)

Palladium-Catalyzed Asymmetric α-Arylation of Alkylnitriles
od: Jiao, Zhiwei, i dr.
Izdano: (2017)

Palladium-Catalyzed Regioselective Arylation of Unprotected Allylamines
od: Vinod G. Landge, i dr.
Izdano: (2020-12-01)

Reactivity of bromoselenophenes in palladium-catalyzed direct arylations
od: Aymen Skhiri, i dr.
Izdano: (2017-12-01)

Palladium-catalyzed cyclobutenation of aryl chlorides with norbornenes
od: Zhenkun Chen, i dr.
Izdano: (2022-02-01)

Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones
od: Jiao, Zhiwei, i dr.
Izdano: (2017)

Intramolecular palladium-catalyzed direct arylation of alkenyl triflates.
od: Cruz, A, i dr.
Izdano: (2007)

Palladium Catalyzed Heck Arylation of 2,3-Dihydrofuran—Effect of the Palladium Precursor
od: Adam Morel, i dr.
Izdano: (2014-06-01)

Intramolecular palladium-catalyzed alkane C-H arylation from aryl chlorides.
od: Rousseaux, S, i dr.
Izdano: (2010)

Pyruvate enolate arylation and alkylation: OBO ester protected pyruvates as useful reagents in organic synthesis
od: Alves Esteves, C, i dr.
Izdano: (2017)

Palladium-catalysed synthesis of isoquinolines
od: Pilgrim, B, i dr.
Izdano: (2011)

Palladium-Catalyzed Conversion of Aryl and Vinyl Triflates to Bromides and Chlorides
od: Shen, Xiaoqiang, i dr.
Izdano: (2012)