ChemInform Abstract: The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis

ChemInform ◽  
2010 ◽  
Vol 33 (16) ◽  
pp. no-no
Author(s):  
Sherry R. Chemler ◽  
Dirk Trauner ◽  
Samuel J. Danishefsky
Keyword(s):  
Natural Product ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Natural Product Synthesis ◽  
Mechanistic Study ◽  
Cross Coupling Reaction

Evidence for “cocktail”-type catalysis in Buchwald–Hartwig reaction. A mechanistic study

2021 ◽  
Author(s):  
Darya O. Prima ◽  
Malena Madiyeva ◽  
Julia V. Burykina ◽  
Mikhail E. Minyaev ◽  
Daniil A. Boiko ◽  
...  
Keyword(s):  
Type System ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Mechanistic Study ◽  
Cross Coupling Reaction

The mechanism of the C–N cross-coupling reaction, catalyzed by Pd/NHC, was evaluated at the molecular and nanoscale levels. The first evidence for the involvement of a “cocktail”-type system in the Buchwald–Hartwig reaction is provided.

scholarly journals Synthesis and Biological Evaluation of Novel 2-Substituted ­Analogues of (–)-Pentenomycin I

Synlett ◽  
2020 ◽  
Vol 31 (05) ◽  
pp. 475-481
Author(s):  
Stavroula A. Zisopoulou ◽  
Spyridon Bousis ◽  
Jörg Haupenthal ◽  
Jennifer Herrmann ◽  
Rolf Müller ◽  
...  
Keyword(s):  
Natural Product ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Eukaryotic Cell ◽  
Biological Evaluation ◽  
Gram Positive Bacteria ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Synthesis And Biological Evaluation ◽  
Derivatives Of

A library of novel 2-substituted derivatives of the antibiotic natural product pentenomycin I is presented. The new collection of analogues is divided in two main classes, 2-alkynyl- and 2-aryl- derivatives, which are accessed by the appropriate type of palladium-catalyzed cross-coupling reaction of the 2-iodo-protected pentenomycin I with suitable nucleophiles. The new derivatives were tested for their activity against certain types of bacteria and one of them, compound 8h, was found to exhibit significant inhibitory activity against several Gram-positive bacteria but also displayed cytotoxic activity against eukaryotic cell lines.

Convergent First Total Synthesis of Melovinone: A Densely Substituted 3-Methoxy-4-quinolone Isolated from Melochia tomentosa L.

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4253-4262
Author(s):  
Abel A. Arroyo Aguilar ◽  
Gabriela N. Ledesma ◽  
Bárbara Tirloni ◽  
Teodoro S. Kaufman ◽  
Enrique L. Larghi
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Nitro Group ◽  
Nmr Spectra ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Full Agreement ◽  
Nitrobenzoic Acid ◽  
Microwave Assisted ◽  
Cross Coupling Reaction

The first total synthesis of melovinone, a nonrutaceous 3-methoxy-4-quinolone alkaloid isolated from Melochia tomentosa L., is reported. The target was acquired in a convergent fashion through the Suzuki–Miyaura cross-coupling reaction between an ortho-nitrobenzoic acid acetonyl ester derivative prepared from vanillin and potassium 5-phenyl-1-pentyltrifluoroborate, obtained from β-phenethyl bromide. The coupling was followed by a chemoselective reduction of the nitro group and a microwave-assisted and AcOH-promoted cyclization with rearrangement of the resulting acetonyl anthranilate. This afforded a pseudane intermediate, which was selectively methylated on the 3-OH. The synthetic pathway enabled to reach the objective in 11 steps and 18% overall yield. The 1H NMR spectra of the synthetic and natural product were in full agreement.

scholarly journals A Concise Synthesis of Isocryptolepine by C–C Cross-Coupling Followed by a Tandem C–H Activation and C–N Bond Formation

SynOpen ◽  
2017 ◽  
Vol 01 (01) ◽  
pp. 0041-0044 ◽  
Author(s):  
Ida Helgeland ◽  
Magne Sydnes
Keyword(s):  
Natural Product ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
Acid Hydrochloride ◽  
Aminophenylboronic Acid

Isocryptolepine (1), a potent antimalarial natural product, was prepared in three steps from 3-bromoquinoline and 2-aminophenylboronic acid hydrochloride. The key transformations were a Suzuki–Miyaura cross-coupling reaction followed by a palladium-initiated intramolecular C–H activation/C–N bond formation between an unprotected amine and an aromatic C–H group. The two key reactions can also be performed in one pot.

Nickel-Catalyzed Acylation of Aryl Bromides with Acyl Imidazoles

2019 ◽  
Author(s):  
Junming Zhuo ◽  
Yong Zhang ◽  
Zijian Li ◽  
Chao Li
Keyword(s):  
Natural Product ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Chain Mechanism ◽  
Radical Chain ◽  
Aryl Bromides ◽  
Cross Coupling Reaction ◽  
Acyl Radicals ◽  
Cost Efficient ◽  
Acylation Reactions

Alkyl imidazolides were herein found to be viable coupling partners for the Ni-catalyzed acylation of aryl bromides. This cross-coupling reaction features a broad substrate scope and be performed in an extremely cost-efficient fashion. Mechanistically, formation of acyl radicals via reduction of imidazolides represents a major departure from other reported radical acylation reactions. Of particular note, extensive studies revealed an intriguing radical chain mechanism and a remarkable CO-extrusion-recombination phenomenon. Finally, the practicality of this cross-coupling was demonstrated with a gram-scale reaction for the synthesis of a furan diterpenoid natural product.

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